Metal catalyzed synthesis of 2-aminobenzamide derivatives

Abstract

An improved method is disclosed for preparing compounds of Formula 1 and Formula 2 comprising reacting a compound of Formula 3 in the presence of a palladium source, a ligand, a base and carbon monoxide wherein R1, R2, R3, R4, R5, R6 and X are as defined in the disclosure. Also disclosed are methods for preparing the compound of Formula 6 wherein R1, R2, R3, R4, R5, Y1, Y2, Y3 and n are as defined in the disclosure, using a compound of Formula 1 characterized by preparing the compound of Formula 1 by the method disclosed above or using a compound of Formula 1 prepared by the method disclosed above.

Description

[0001]METAL CATALYZED SYNTHESIS OF 2-AMINOBENZAMIDE DERIVATIVES CROSS-REFERENCE TO RELATED APPLICATION This application claims the benefit of U.S. Provisional Application No.63 / 561854, filed March 06, 2024, all of which is incorporated by reference herein in its entirety. FIELD This disclosure relates to an improved method for preparing 2-aminobenzamides and derivatives thereof. Such compounds prepared by the method disclosed herein are useful for the preparation of diamide crop protection agents that are of interest as insecticides, such as for example chlorantraniliprole, cyantraniliprole and derivatives thereof. BACKGROUND Preparation of certain 2-aminobenzamides and their utility as intermediates for preparing insecticidal anthranilic diamides is disclosed in PCT Patent Publication WO2006 / 062978. Catalytic reactions are known to be useful as an alternative way to conduct certain reactions. For example, a method for preparing 2-aminobenzamides was disclosed in PCT Patent Publication WO2012 / 103436. The disclosed method, however, requires relatively large loadings of expensive palladium based catalysts. The improved method disclosed herein allows for lower catalyst loadings with either a soluble palladium source used at low levels or a supported palladium source that can be readily recycled. The present disclosure provides novel methods useful for preparing 2-aminobenzamides. Benefits of the methods of the present disclosure compared to previous methods include a significant improvement in operating the process on a commercial scale by using a lower effective catalyst loading while maintaining a high conversion of starting material within an acceptable period of time. SUMMARY This disclosure is directed to a method for preparing a compound of Formula 1 wherein R1is F, Cl, cyano, C1–C4alkyl, C1–C4haloalkyl, C1–C4alkoxy or C1–C6haloalkoxy; R2is H, F, Cl or cyano; R3is F, Cl or cyano; R4is H, F, Cl or cyano; R5is H, C1–C4alkyl, C3–C6cycloalkyl, C4–C7cycloalkylalkyl, C4–C7alkylcycloalkyl or cyclopropylcyclopropyl; and the method comprising: (I) forming a mixture comprising: (A) a compound of Formula 2 , wherein R1is F, Cl, C1–C4alkyl, C1–C4haloalkyl, C1–C4alkoxy or C1–C6haloalkoxy; R2is H, F, Cl or cyano; R3is F, Cl or cyano; R4is H, F, Cl or cyano; R6is C1–C14alkyl, C2–C14hydroxyalkyl, C3–C14dialkylaminoalkyl, or C3– C14halodialkylaminoalkyl); and wherein the compound of Formula 2 is prepared to a method comprising: (1) forming a mixture comprising: (a) a compound of Formula 3 , wherein R1is F, Cl, C1–C4alkyl, C1–C4haloalkyl, C1–C4alkoxy or C1–C6haloalkoxy; R2is H, F, Cl or cyano; R3is F, Cl or cyano; R4is H, F, Cl or X is Br or I; and (b) a palladium source; (c) a ligand; (d) a base; (e) carbon monoxide; and (f) a compound of Formula 4 , wherein R6is C1–C14alkyl, C2–C14hydroxyalkyl, C3–C14dialkylaminoalkyl, or C3–C14halodialkylaminoalkyl); and (2) reacting the mixture; and (B) a compound of Formula 5 , wherein R5is H, C1–C4alkyl, C3–C6cycloalkyl, C4–C7cycloalkylalkyl, C4–C7alkylcycloalkyl or cyclopropylcyclopropyl; and (II) reacting the mixture. Also disclosed is a method of preparing compound of Formula 2 , R1is F, Cl, C1–C4alkyl, C1–C4haloalkyl, C1–C4alkoxy or C1–C6haloalkoxy; R2is H, F, Cl or cyano; R3is F, Cl or cyano; R4is H, F, Cl or cyano; R6is C1–C14alkyl, C2–C14C3–C14dialkylaminoalkyl, or C3– C14; and wherein the compound of Formula 2 is prepared to a method comprising: (1) forming a mixture comprising: (a) a compound of Formula 3 , wherein R1is F, Cl, C1–C4alkyl, C1–C4haloalkyl, C1–C4alkoxy or C1–C6haloalkoxy; R2is H, F, Cl or cyano; R3is F, Cl or cyano; R4is H, F, Cl or cyano; X is Br or I; and (b) a palladium source; (c) a ligand; (d) a base; (e) carbon monoxide; and (f) a compound of Formula 4 , wherein R6is C1–C14alkyl, C2–C14hydroxyalkyl, C3–C14dialkylaminoalkyl, or C3–C14halodialkylaminoalkyl); and (2) reacting the mixture. This disclosure is also directed to a of preparing a diamide compound of Formula 6 , wherein Y1is a halogen or C1–C4haloalkyl; Y2is hydrogen, halogen, cyano, C1-C4alkyl or C1-C4haloalkyl; each Y3is independently halogen, cyano, C1-C4alkyl or C1-C4haloalkyl; n is 0, 1, 2 or 3; R1is F, Cl, C1–C4alkyl, C1–C4haloalkyl, C1–C4alkoxy or C1–C6haloalkoxy; R2is H, F, Cl or cyano; R3is F, Cl or cyano; R4is H, F, Cl or cyano; R5is H, C1–C4alkyl, C3–C6cycloalkyl, C4–C7cycloalkylalkyl, C4–C7alkylcycloalkyl or cyclopropylcyclopropyl; using a compound of Formula 1 , of Formula 1 by the method disclosed above. DETAILED DESCRIPTION The method of this disclosure is generally applicable to a wide range of compounds of Formula 1, 2 and 3. In the recitations herein, although the R1, R2, R3and R4substituents are connected to the backbone of the phenyl ring, the R1, R2, R3and R4substituents are separated from the reaction center. The R1, R2, R3and R4substituents can encompass a variety of groups preparable by modern methods of organic chemistry. One skilled in the art will recognize that certain groups are to the reagents of this method and may be transformed under the reaction conditions. As used herein, the terms “comprises,” “comprising,” “includes,” “including,” “has,” “having,” “contains”, “containing,” “characterized by” or any other variation thereof, are intended to cover a non-exclusive inclusion, subject to any limitation explicitly indicated. For example, a composition, mixture, process or method that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such composition, mixture, process or method. The transitional phrase “consisting of” excludes any element, step, or ingredient not specified. If in the claim, such phrase would close the claim to the inclusion of materials other than those expressly recited except for impurities ordinarily associated therewith. When the phrase “consisting of” appears in a clause of the body of a claim, rather than immediately following the preamble, it limits only the element set forth in that clause; other elements are not excluded from the claim as a whole. The transitional phrase “consisting essentially of” is used to define a composition, process or method that includes materials, steps, features, components, or elements, in addition to those literally disclosed, provided that these additional materials, steps, features, components, or elements do not materially affect the basic and novel characteristic(s) of the disclosure. The term “consisting essentially of” occupies a middle ground between “comprising” and “consisting of”. Where applicants have defined an embodiment or a portion thereof with an open-ended term such as “comprising,” it should be readily understood that (unless otherwise stated) the description should be interpreted to also describe such an embodiment using the terms “consisting essentially of” or “consisting of.” Further, unless expressly stated to the contrary, “or” refers to an inclusive or and not to an exclusive or. For example, a condition A or B is satisfied by any one of the following: A is true (or present) and B is false (or not present), A is false (or not present) and B is true (or present), and both A and B are true (or present). Also, the indefinite articles “a” and “an” preceding an element or component of the disclosure are intended to be nonrestrictive regarding the number of instances (i.e., occurrences) of the element or component. Therefore “a” or “an” should be read to include one or at least one, and the singular word form of the element or component also includes the plural unless the number is obviously meant to be singular. As used herein, the term "alkyl", used either alone or in compound words such as "haloalkyl," "alkylcycloalkyl," "cycloalkylalkyl" or "alkylcycloalkylalkyl," includes straight-chain or branched alkyl groups having one to four carbon atoms, e.g., methyl, ethyl, n-propyl, i-propyl, or the different butyl isomers. The term "Alkoxy" denotes alkyl attached to and linked through an oxygen atom as, for example, methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butoxy "Hydroxyalkyl" denotes an alkyl group substituted with one hydroxy group. Examples of "hydroxyalkyl" include HOCH2CH2, CH3CH2(OH)CH and HOCH2CH2CH2CH2. The term “cycloalkyl” denotes a saturated carbocyclic ring consisting of 3 to 6 carbon atoms linked to one another by single bonds. Examples of “cycloalkyl” include cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. The term “cycloalkylalkyl” denotes cycloalkyl substitution on an alkyl moiety. Examples of “cycloalkylalkyl” include cyclopropylmethyl, cyclopentylethyl and other cycloalkyl moieties bonded to straight-chain or branched alkyl groups. The term “alkylcycloalkyl” denotes alkyl substitution on a cycloalkyl moiety and includes, for example, 1-methylcyclopropyl, i-propylcyclobutyl, 3-methylcyclopentyl and 4-methylcyclohexyl. “Alkylcycloalkylalkyl” denotes alkylcycloalkyl substitution on an alkyl moiety. Examples of “alkylcycloalkylalkyl” include methylcyclohexylmethyl and ethylcycloproylmethyl. The term “cyclopropylcyclopropyl,” denotes cyclopropyl substitution on another cyclopropyl ring. Examples of “cyclopropylcyclopropyl,” include 1,1'- bicyclopropyl-1-yl, 1,1'-bicyclopropyl-2-yl and the different cis- and trans- cyclopropylcyclopropyl isomers such as (1R,2S)-1,1'-bicyclopropyl-2-yl and (1R,2R)-1,1'- bicyclopropyl-2-yl. The term “dialkylaminoalkyl” denotes two independent straight-chain or branched alkyl moieties bonded to a nitrogen atom of an amino(straight-chain or branched)alkyl moiety. Examples of “dialkylaminoalkyl” include (CH3)2NCH2-, (CH3)2CH(CH3)NCH2- and (CH3)2NCH(CH3)-. The term “halogen”, either alone or in compound words such as “haloalkyl” or “haloalkoxy”, includes fluorine, chlorine, bromine or iodine. Furthermore, when used in compound words such as “haloalkyl”, said alkyl may be partially or fully substituted with halogen atoms which may be the same or different. Examples of “haloalkyl” include F3C, ClCH2, CF3CH2and CF3CCl2. Examples of “haloalkoxy” include CF3O-, CCl3CH2O-, HCF2CH2CH2O- and CF3CH2O-. The chemical abbreviations C(O) and C(=O) as used herein represent a carbonyl moiety. The chemical abbreviations CO2, C(O)O and C(=O)O as used herein represent an oxycarbonyl moiety. The chemical abbreviations S(O) and S(=O) as used herein represent a sulfinyl moiety. The chemical abbreviations SO2, S(O)2and S(=O)2as used herein represent a sulfonyl moiety. The chemical abbreviations C(S) and C(=S) as used herein represent a thiocarbonyl moiety. "CHO" means formyl. The total number of carbon atoms in a substituent group is indicated by the “Ch-C1” prefix where h and i are numbers from 1 to 14. For example, C1-C4alkoxy designates CH3O- through CH3CH2CH2CH2O-; C3–C6cycloalkyl designates cyclopropane through cyclohexane; C5alkylcycloalkylalkyl designates, for example, -CH2C(CH3)(-CH2CH2-) or -CH2C(-CH(CH3)CH2-); designates, for example, -CH2CH2C(CH3)(-CH2CH2-), - (-CH(CH3)CH2-), -CH2C(CH2CH3)(-C H2CH2-), -CH2C(-CH(CH2CH3)CH2-), -CH2C(CH3)(-CH2CH2CH2-), -CH2C(-CH(CH3)C H2CH2-) or -CH2C(-CH2CH(CH3)CH2-); and C8alkylcycloalkylalkyl designates the various isomers of an alkyl group substituted with an alkylcycloalkyl group containing a combined total of eight carbon atoms. As used herein, the term "suitable" indicates that the entity so described is appropriate for use in the situation or circumstance indicated. The term "reacting" and the like refer to adding, contacting, or mixing two or more reagents under appropriate conditions to produce the indicated and / or the desired product. It should be appreciated that the reaction which produces the indicated and / or the desired product may not necessarily result directly from the combination of two reagents which were initially added. One or more intermediates may be produced in the mixture which ultimately leads to the formation of the indicated and / or the desired product. Reacting can take place in the presence or absence of solvent, at a temperature above room temperature or below room temperature, under an inert atmosphere, etc. The term "optionally" when used herein means that the optional condition may or may not be present. For example, when a reaction is conducted optionally in the presence of an organic acid, the organic acid may or may not be present. The term “combining” when used to describe a chemical reaction describes the act of “contacting” the referenced chemicals with each other, or alternatively “reacting” the chemicals with each other. As used herein, the term “ligand” refers to an organic molecule comprising at least one pair of electrons available for coordination with a metal atom (in this case a palladium atom). Ligands in general can be neutral or charged, and can be unidentate, bidentate or higher. The term "salt" or "salts", as used herein, refers to any anionic and cationic complex. Yield in the context of the present disclosure refers to either the isolated yield or the yield calculated by the Area% determined by HPLC analysis. Yield calculations are expressed as moles of desired product formed divided by moles that would have been formed if there were no side reactions and the limiting reactant was fully converted to the desired product. Selectivity in the context of the present disclosure is expressed as moles of desired product formed divided by the moles of starting material consumed. The amount of starting material consumed is represented by moles of the starting material minus the moles of the remaining starting material. The term “catalyst loading” in the context of the present disclosure refers to the amount of catalyst, expressed in mol%, versus the starting material used in a single reaction. The term “effective catalyst loading” in the context of the present disclosure refers to the amount of catalyst, expressed in mol%, versus the starting material used in repeated reactions (i.e. “catalyst loading” divided by the sum of initial reaction plus recycled reactions wherein the catalyst was utilized). In the present disclosure, ratios are generally recited as single numbers, which are relative to the number 1; for example, a ratio of 4 means 4 : 1. In the present disclosure the term “mole ratio” refers to the number of moles of the specified reagent relative to the other specified reagent. Alternatively, the ratio may be expressed as a “mole percentage” which express the mole ratio as a percentage (i.e., mole ratio / 100). It also is understood that any numerical range recited herein includes all values from the lower value to the upper value. For example, if a numerical range is stated as 1 to 10, it is intended that values such as 2 to 9, 2.5 to 8.1, or 1 to 1.6, etc., are expressly enumerated in this specification. These are only examples of what is specifically intended, and all possible combinations of numerical values between and including the lowest value and the highest value enumerated are to be considered to be expressly stated in this application. It is further understood that if a range is recited in the "from / to" or "from about / to about" format, such as from 10:1 to 1:10, the range includes the endpoints (i.e., 10:1 and 1:10). As used herein, the term "about" means plus or minus 10% of the value. Embodiments of the present disclosure as described in the Summary include those described below. In the following Embodiments, reference to "a compound of Formula 1" includes the definitions of substituents specified in the Summary unless further defined in the Embodiments. Embodiments of the present disclosure include: Embodiment A1. The method described in the Summary for preparing a compound of Formula 1 wherein R1is F, Cl, CN or C1–C4alkyl. Embodiment A2. The method of Embodiment A1 wherein R1is F, Cl, methyl or ethyl. Embodiment A3. The method of Embodiment A2 wherein R1is F, Cl or methyl. Embodiment A4. The method of Embodiment A3 wherein R1is Cl or methyl. Embodiment A5. The method of Embodiment A1 wherein R1is C1–C4alkyl. Embodiment A5a. The method of Embodiment A4 or Embodiment A5 wherein R1is methyl. Embodiment A6. The method of any one of Embodiments A1 through A5a wherein R2is H, F or Cl. Embodiment A7. The method Embodiment A6 wherein R2is H. Embodiment A8. The method of any one of Embodiments A1 through A7 wherein R3is chloro or cyano. Embodiment A9. The method Embodiment A8 wherein R3is chloro. Embodiment A10. The method Embodiment A8 wherein R3is cyano. Embodiment A11. The method of any of Embodiments A1 through A10 wherein R4is H, F or Cl. Embodiment A12. The method Embodiment A11 wherein R4is H. Embodiment A13. The method Embodiment A11 wherein R4is Cl. Embodiment A14. The method Embodiment A11 wherein R4is F. Embodiment A15. The method of any one of Embodiments A1 through A12 wherein R5is H, methyl, isopropyl, cyclopropyl, cyclobutyl, cyclopropylmethyl, methylcyclopropyl or cyclopropylcyclopropyl. Embodiment A16. The method of Embodiment A15 wherein R5is H, methyl, isopropyl, cyclopropyl, cyclopropylmethyl or cyclopropylcyclopropyl. Embodiment A17. The method of Embodiment A16 wherein R5is H, methyl, isopropyl or cyclopropylcyclopropyl. Embodiment A18. The method of Embodiment A17 wherein R5is H, methyl or isopropyl. Embodiment A19. The method of Embodiment A18 wherein R5is H. Embodiment A20. The method of Embodiment A18 wherein R5is methyl. Embodiment A21. The method of Embodiment A18 wherein R5is isopropyl. Embodiment A22. The method of any one of Embodiments A1 through A21 wherein R6is C1–C14alkyl, C2–C14hydroxyalkyl or C3–C14dialkylaminoalkyl. Embodiment A23. The method of Embodiment A22 wherein R6is methyl, ethyl, isopropyl, hydroxyethyl, hydroxypropyl or dimethylaminoethyl. Embodiment A24. The method of Embodiment A22 wherein R6is methyl, ethyl, isopropyl, hydroxyethyl or dimethylaminoethyl. Embodiment A25. The method of Embodiment A22 wherein R6is hydroxyethyl or dimethylaminoethyl. Embodiment A26. The method of Embodiment A22 wherein R6is hydroxyethyl. Embodiment A27. The method of Embodiment A22 wherein R6is dimethylaminoethyl. Embodiment A28. The method of any one of Embodiments A1 through A27 wherein X is Br. Embodiment A29. The method of any one of Embodiments A1 through A27 wherein X is I. Embodiment A30. The method of any one of Embodiments A1 through A29 wherein the compound of Formula 1 is 2-amino-5-chloro-N,3-dimethyl-benzamide or 2-amino-5-cyano-N,3-dimethyl-benzamide. Embodiment A31. The method Embodiment A30 wherein the compound of Formula 1 is 2-amino-5-chloro-N,3-dimethyl-benzamide. Embodiment A31a. The method A30 wherein the compound of Formula 1 is the compound of Formula 1a . Embodiment A32. The A1 through A31 wherein the compound of 2-amino-5-chloro-3- methylbenzoate or 2-hydroxyethyl 2-amino-5-cyano-3-methylbenzoate. Embodiment A33. The method Embodiment A30 wherein the compound of Formula 2 is 2-hydroxyethyl 2-amino-5-chloro-3-methylbenzoate. Embodiment A33a. The method Embodiment A30 wherein the compound of Formula 2 is the compound of Formula 2a . Embodiment A33b. The the compound of Formula 3 is a compound of Formula 3a . A1 through A33 wherein the palladium source is a soluble palladium compound or a palladium source on an insoluble support. Embodiment A35. The method of Embodiment A34 wherein the palladium source is a soluble palladium compound. Embodiment A35a. The method of A35 wherein the palladium source is a soluble palladium compound from palladium(II) acetate, palladium(II) trifluoroacetate, palladium(II) propionate, palladium(II) benzoate, palladium(II) chloride, palladium(II) bromide, palladium(II) sulfate, (dibenzylideneacetone)- dipalladium(0) and palladium(II) acetylacetonate. Embodiment A35b. The method of Embodiment A35 wherein the palladium source is a soluble palladium compound selected from palladium(II) acetate, palladium(II) chloride, palladium(II) bromide, and palladium(II) acetylacetonate. Embodiment A35c. The method of Embodiment A35 wherein the palladium source is a soluble palladium compound selected from palladium(II) acetate and palladium(II) chloride. Embodiment A35d. The method of Embodiment A35 wherein the palladium source is palladium(II) acetate. Embodiment A35e. The method of Embodiment A35 wherein the palladium source is palladium(II) chloride. Embodiment A36. The method of Embodiment A34 wherein the palladium source is a palladium source on an insoluble support. Embodiment A36a. The method of Embodiment A36 wherein the palladium source on an insoluble support is selected from palladium on carbon, palladium (II) hydroxide on carbon, palladium on barium sulfate, and palladium on alumina. Embodiment A36b. The method of Embodiment A36 wherein the palladium source on an insoluble support is palladium on carbon. Embodiment A36c. The method of Embodiment A36 wherein the palladium source on an insoluble support is palladium (II) hydroxide on carbon. Embodiment A36d. The method of Embodiment A36 wherein the palladium source on an insoluble support further comprising the steps: (3) separating the reacted palladium source from the mixture, after Step (2) reacting the mixture; (4) recycling the separated palladium source of Step (3) to Step (1) as (b) the palladium source; and (5) repeating Steps (1) through (3) using the recycled palladium source at least one time. Embodiment A36e. The method of Embodiment A36d wherein Steps (1) through (3) are repeated 1 to 50 times using the recycled palladium source. Embodiment A36f. The method of Embodiment A36d wherein Steps (1) through (3) are repeated 1 to 20 times using the recycled palladium source. Embodiment A36g. The method of Embodiment A36d wherein Steps (1) through (3) are repeated 1 to 15 times using the recycled palladium source. Embodiment A36h. The method of A36d wherein Steps (1) through (3) are repeated 1 to 10 times recycled palladium source. Embodiment A36i. The method of Embodiment A36d wherein Steps (1) through (3) are repeated 1 to 6 times using the recycled palladium source. Embodiment A37. The method of any one of Embodiments A1 through A36 wherein the effective catalyst loading of the palladium source relative to the compound of Formula 3 is less than 0.1 mol%. Embodiment A38. The method of Embodiment A37 wherein the effective catalyst loading of the palladium source relative to the compound of Formula 3 is between 0.0001 and 0.099 mol%. Embodiment A39. The method of Embodiment A37 wherein the effective catalyst loading of the palladium source relative to the compound of Formula 3 is between 0.001 and 0.099 mol%. Embodiment A40. The method of Embodiment A37 wherein the effective catalyst loading of the palladium source relative to the compound of Formula 3 is between 0.005 and 0.099 mol%. Embodiment A41. The method of Embodiment A37 wherein the effective catalyst loading of the palladium source relative to the compound of Formula 3 is between 0.05 and 0.099 mol%. Embodiment A42. The method of Embodiment A37 wherein the effective catalyst loading of the palladium source relative to the compound of Formula 3 is between 0.02 and 0.099 mol%. Embodiment A43. The method of Embodiment A37 wherein the effective catalyst loading of the palladium source relative to the compound of Formula 3 is between about 0.01 and 0.099 mol%. Embodiment A44. The method of any one of Embodiments A1 through A43 wherein the ligand is a bidentate bisphosphine ligand. Embodiment A45. The method of Embodiment A44 wherein the ligand is a bidentate bisphosphine ligand selected from 1,1'-bis(diphenylphosphino)ferrocene, 1,4-bis(diphenylphosphino)butane, 1,1’-bis(diphenylphosphino)propane, and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene. Embodiment A46. The method of Embodiment A45 wherein the ligand is a bidentate bisphosphine ligand selected from 1,1'-bis(diphenylphosphino)ferrocene, 1,4-bis(diphenylphosphino)butane, and 1,1’-bis(diphenylphosphino)propane. Embodiment A47. The method of Embodiment A45 wherein the ligand is 1,1'-bis(diphenylphosphino)ferrocene. Embodiment A48. The method of Embodiment A45 wherein the ligand is 1,4-bis(diphenylphosphino)butane. Embodiment A49. The method of A45 wherein the ligand is 1,1’-bis(diphenylphosphino)propane. Embodiment A50. The method of any one of Embodiments A1 through A49 wherein the mole ratio of the palladium to ligand is at least about 1:0.5. Embodiment A51. The method of Embodiment A50 wherein the mole ratio of the palladium to ligand is at least about 1:1. Embodiment A52. The method of Embodiment A50 wherein the mole ratio of the palladium to ligand is between about 1:0.5 and 1:100. Embodiment A53. The method of Embodiment A50 wherein the mole ratio of the palladium to ligand is between about 1:0.5 and 1:10. Embodiment A53a. The method of Embodiment A53 wherein the mole ratio of the palladium to ligand is between about 1:5 and 1:10. Embodiment A54. The method of Embodiment A50 wherein the mole ratio of the palladium to ligand is between about 1:0.5 and 1:5. Embodiment A55. The method of Embodiment A50 wherein the mole ratio of the palladium to ligand is between about 1:1 and 1:5. Embodiment A56. The method of any one of Embodiments A1 through A55 wherein the base is an organic base or an inorganic base. Embodiment A57. The method of Embodiment A56 wherein the base is an organic base selected from trimethylamine, triethylamine, tributylamine and N,N-dimethylisopropylamine. Embodiment A58. The method of Embodiment A56 wherein the base is an organic base selected from triethylamine and tributylamine. Embodiment A59. The method of Embodiment A56 wherein the base is triethylamine. Embodiment A60. The method of Embodiment A56 wherein the base is an inorganic base selected from sodium carbonate, sodium bicarbonate, sodium hydroxide, calcium hydroxide, cesium hydroxide, potassium hydroxide and potassium phosphate. Embodiment A61. The method of Embodiment A60 wherein the base is an inorganic base selected from sodium carbonate, sodium bicarbonate and sodium hydroxide. Embodiment A62. The method of Embodiment A61 wherein the base is sodium carbonate. Embodiment A63. The method of Embodiment A61 wherein the base is sodium bicarbonate. Embodiment A64. The method of any one of Embodiments A1 through A63 wherein the mole ratio of the base to a compound of Formula 3 is at least about 1. Embodiment A65. The method of Embodiment A64 wherein the mole ratio of the base to a compound of Formula 3 is at least about 1.5. Embodiment A66. The method of A64 wherein the mole ratio of the base to a compound of Formula 3 is than about 5. Embodiment A67. The method of Embodiment A64 wherein the mole ratio of the base to a compound of Formula 3 is between about 1 and 5. Embodiment A68. The method of Embodiment A64 wherein the mole ratio of the base to a compound of Formula 3 is between about 1 and 3. Embodiment A69. The method of Embodiment A64 wherein the mole ratio of the base to a compound of Formula 3 is between about 1.5 and 3. Embodiment A70. The method of any one of Embodiments A1 through A69 wherein the method is performed in a suitable solvent. Embodiment A71. The method of Embodiment A70 wherein the method is performed in a suitable solvent comprising one or more organic solvents selected from ethers, nitriles, aromatic hydrocarbons, amides, alcohols and amino-alcohols. Embodiment A72. The method of Embodiment A70 wherein the method is performed in a suitable solvent comprising one or more organic solvents selected from tetrahydrofuran, 2,5,8-trioxanonane, acetonitrile, xylenes, toluene, N,N-dimethylformamide, N,N-dimethylacetamide, methanol, ethylene glycol and N,N-dimethylethanolamine. Embodiment A73. The method of Embodiment A72 wherein the method is performed in a suitable solvent comprising ethylene glycol. Embodiment A74. The method of Embodiment A72 wherein the method is performed in a suitable solvent comprising N,N-dimethylethanolamine. Embodiment A75. The method of Embodiment A72 wherein the method is performed in a suitable solvent comprising a mixture of ethylene glycol and N,N-dimethylethanolamine. Embodiment A76. The method of Embodiment A72 wherein the method is performed in a suitable solvent consisting of ethylene glycol and N,N-dimethylethanolamine. Embodiment A77. The method of any one of Embodiments A1 through A76 wherein the method is performed at a pressure of at least about 15 psi (about 0.10 MPa) of carbon monoxide. Embodiment A78. The method of Embodiment A77 wherein the method is performed at a pressure of at least about 40 psi (about 0.27 MPa) of carbon monoxide. Embodiment A79. The method of Embodiment A78 wherein the method is performed at a pressure of at least about 70 psi (about 0.48 MPa) of carbon monoxide. Embodiment A80. The method of Embodiment A79 wherein the method is performed at a pressure between about 70 psi and 225psi (about 0.48 to 1.5 MPa) of carbon monoxide. Embodiment A81. The method of any of Embodiments A1 through A80 wherein the method is performed at a greater than 70 °C. Embodiment A82. The method of Embodiment A81 wherein the method is performed at a temperature between about 70 °C and about 150 °C. Embodiment A83. The method of Embodiment A81 wherein the method is performed at a temperature between about 80 °C and about 120 °C. Embodiment A84. The method of Embodiment A81 wherein the method is performed at a temperature between about 100 °C and about 120 °C. Embodiment B1. The method described in the Summary for preparing a compound of Formula 2 , wherein R1is F, Cl, C1–C4alkyl, C1–C4haloalkyl, C1–C4alkoxy or C1–C6haloalkoxy; R2is H, F, Cl or cyano; R3is F, Cl or cyano; R4is H, F, Cl or cyano; R6is C1–C14alkyl, C2–C14hydroxyalkyl, C3–C14dialkylaminoalkyl, or C3– C14halodialkylaminoalkyl); and the method comprising: (1) forming a mixture comprising: (a) a compound of Formula 3 , wherein R1is F, Cl, C1–C4alkyl, C1–C4haloalkyl, C1–C4alkoxy or C1–C6haloalkoxy; R2is H, F, Cl or R3is F, Cl or cyano; R4is H, F, Cl or cyano; X is Br or I; and (b) a palladium source; (c) a ligand; (d) a base; (e) carbon monoxide; and (f) a compound of Formula 4 , wherein R6is C1–C14alkyl, C2–C14hydroxyalkyl, C3–C14dialkylaminoalkyl, or C3–C14halodialkylaminoalkyl); and (2) reacting the mixture. Embodiment B2. The method of Embodiment B1 wherein R1is F, Cl, CN or C1–C4alkyl. Embodiment B3. The method of Embodiment B2 wherein R1is F, Cl, methyl or ethyl. Embodiment B4. The method of Embodiment B3 wherein R1is F, Cl or methyl. Embodiment B5. The method of Embodiment B4 wherein R1is Cl or methyl. Embodiment B6. The method of Embodiment B2 wherein R1is C1–C4alkyl. Embodiment B6a. The method of Embodiment B5 or Embodiment B6 wherein R1is methyl. Embodiment B7. The method of any one of Embodiments B1 through B6a wherein R2is H, F or Cl. Embodiment B8 The method Embodiment B7 wherein R2is H. Embodiment B9. The method of any one of Embodiments B1 through B8 wherein R3is chloro or cyano. Embodiment B10. The method Embodiment B9 wherein R3is chloro. Embodiment B11. The method Embodiment B9 wherein R3is cyano. Embodiment B12. The method of any one of Embodiments B1 through B11 wherein R4is H, F or Cl. Embodiment B13. The method Embodiment B12 wherein R4is H. Embodiment B14. The method Embodiment B12 wherein R4is Cl. Embodiment B15. The method Embodiment B12 wherein R4is F. Embodiment B16. The method of any one of Embodiments B1 through B15 wherein R6is C1–C14alkyl, C2–C14hydroxyalkyl or C3–C14dialkylaminoalkyl. Embodiment B17. The method of B16 wherein R6is methyl, ethyl, isopropyl, hydroxyethyl, or dimethylaminoethyl. Embodiment B18. The method of Embodiment B16 wherein R6is methyl, ethyl, isopropyl, hydroxyethyl or dimethylaminoethyl. Embodiment B19. The method of Embodiment B16 wherein R6is hydroxyethyl or dimethylaminoethyl. Embodiment B20. The method of Embodiment B16 wherein R6is hydroxyethyl. Embodiment B21. The method of Embodiment B16 wherein R6is dimethylaminoethyl. Embodiment B22. The method of any one of Embodiments B1 through B21 wherein X is Br. Embodiment B23. The method of any one of Embodiments B1 through B21 wherein X is I. Embodiment B24. The method of any one of Embodiments B1 through B23 wherein the compound of Formula 2 is 2-hydroxyethyl 2-amino-5-chloro-3- methylbenzoate or 2-hydroxyethyl 2-amino-5-cyano-3-methylbenzoate. Embodiment B25. The method Embodiment B24 wherein the compound of Formula 2 is 2-hydroxyethyl 2-amino-5-chloro-3-methylbenzoate. Embodiment B25a. The method Embodiment B24 wherein the compound of Formula 2 is the compound of Formula 2a . Embodiment B26. The B1 through B24 wherein the compound of Formula 3 is a compound of Formula 3a . Embodiment B27. The method of any one of Embodiments B1 through B26 wherein the palladium source is a soluble palladium compound or a palladium source on an insoluble support. Embodiment B28. The method of B27 wherein the palladium source is a soluble palladium compound. Embodiment B28a. The method of Embodiment B28 wherein the palladium source is a soluble palladium compound selected from palladium(II) acetate, palladium(II) trifluoroacetate, palladium(II) propionate, palladium(II) benzoate, palladium(II) chloride, palladium(II) bromide, palladium(II) sulfate, (dibenzylideneacetone)- dipalladium(0) and palladium(II) acetylacetonate. Embodiment B28b. The method of Embodiment B28 wherein the palladium source is a soluble palladium compound selected from palladium(II) acetate, palladium(II) chloride, palladium(II) bromide, and palladium(II) acetylacetonate. Embodiment B28c. The method of Embodiment B28 wherein the palladium source is a soluble palladium compound selected from palladium(II) acetate and palladium(II) chloride. Embodiment B28d. The method of Embodiment B28 wherein the palladium source is palladium(II) acetate. Embodiment B28e. The method of Embodiment B28 wherein the palladium source is palladium(II) chloride. Embodiment B29. The method of Embodiment B27 wherein the palladium source is a palladium source on an insoluble support. Embodiment B29a. The method of Embodiment B29 wherein the palladium source on an insoluble support is selected from palladium on carbon and palladium (II) hydroxide on carbon. Embodiment B29b. The method of Embodiment B29 wherein the palladium source on an insoluble support is palladium on carbon. Embodiment B29c. The method of Embodiment B29 wherein the palladium source on an insoluble support is palladium (II) hydroxide on carbon. Embodiment B29d. The method of Embodiment A29 wherein the palladium source on an insoluble support further comprising the steps: (3) separating the reacted palladium source from the mixture, after Step (2) reacting the mixture; (4) recycling the separated palladium source of Step (3) to Step (1) as (b) the palladium source; and (5) repeating Steps (1) through (3) using the recycled palladium source at least one time. Embodiment B29e. The method of Embodiment B29d wherein Steps (1) through (3) are repeated 1 to 50 times using the recycled palladium source. Embodiment B29f. The method of Embodiment B29d wherein Steps (1) through (3) are repeated 1 to 20 times using the recycled palladium source. Embodiment B29g. The method of B29d wherein Steps (1) through (3) are repeated 1 to 15 times recycled palladium source. Embodiment B29h. The method of Embodiment B29d wherein Steps (1) through (3) are repeated 1 to 10 times using the recycled palladium source. Embodiment B29i. The method of Embodiment B29d wherein Steps (1) through (3) are repeated 1 to 6 times using the recycled palladium source. Embodiment B30. The method of any one of Embodiments B1 through B29 wherein the effective catalyst loading of the palladium source relative to the compound of Formula 3 is less than 0.1 mol%. Embodiment B31. The method of Embodiment B30 wherein the effective catalyst loading of the palladium source relative to the compound of Formula 3 is between 0.0001 and 0.099 mol%. Embodiment B32. The method of Embodiment B30 wherein the effective catalyst loading of the palladium source relative to the compound of Formula 3 is between 0.001 and 0.099 mol%. Embodiment B33. The method of Embodiment B30 wherein the effective catalyst loading of the palladium source relative to the compound of Formula 3 is between 0.005 and 0.099 mol%. Embodiment B34. The method of Embodiment B30 wherein the effective catalyst loading of the palladium source relative to the compound of Formula 3 is between 0.05 and 0.099 mol%. Embodiment B35. The method of Embodiment B30 wherein the effective catalyst loading of the palladium source relative to the compound of Formula 3 is between 0.02 and 0.099 mol%. Embodiment B36. The method of Embodiment B30 wherein the effective catalyst loading of the palladium source relative to the compound of Formula 3 is between about 0.01 and 0.099 mol%. Embodiment B37. The method of any one of Embodiments B1 through B36 wherein the ligand is a bidentate bisphosphine ligand. Embodiment B38. The method of Embodiment B37 wherein the ligand is a bidentate bisphosphine ligand selected from 1,1'-bis(diphenylphosphino)ferrocene, 1,4-bis(diphenylphosphino)butane, 1,1’-bis(diphenylphosphino)propane, and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene. Embodiment B39. The method of Embodiment B38 wherein the ligand is a bidentate bisphosphine ligand selected from 1,1'-bis(diphenylphosphino)ferrocene, 1,4-bis(diphenylphosphino)butane, and 1,1’-bis(diphenylphosphino)propane. Embodiment B40. The method of Embodiment B38 wherein the ligand is 1,1'-bis(diphenylphosphino)ferrocene. Embodiment B41. The method of B38 wherein the ligand is 1,4-bis(diphenylphosphino) Embodiment B42. The method of Embodiment B38 wherein the ligand is 1,1’-bis(diphenylphosphino)propane. Embodiment B43. The method of any one of Embodiments B1 through B42 wherein the mole ratio of the palladium to ligand is at least about 1:0.5. Embodiment B44. The method of Embodiment B43 wherein the mole ratio of the palladium to ligand is at least about 1:1. Embodiment B45. The method of Embodiment B43 wherein the mole ratio of the palladium to ligand is between about 1:0.5 and 1:100. Embodiment B46. The method of Embodiment B43 wherein the mole ratio of the palladium to ligand is between about 1:0.5 and 1:10. Embodiment B46a. The method of Embodiment B46 wherein the mole ratio of the palladium to ligand is between about 1:5 and 1:10. Embodiment B47. The method of Embodiment B43 wherein the mole ratio of the palladium to ligand is between about 1:0.5 and 1:5. Embodiment B48. The method of Embodiment B43 wherein the mole ratio of the palladium to ligand is between about 1:1 and 1:5. Embodiment B49. The method of any one of Embodiments B1 through B48 wherein the base is an organic base or an inorganic base. Embodiment B50. The method of Embodiment B49 wherein the base is an organic base selected from trimethylamine, triethylamine, tributylamine and N,N-dimethylisopropylamine. Embodiment B51. The method of Embodiment B49 wherein the base is an organic base selected from triethylamine and tributylamine. Embodiment B52. The method of Embodiment B49 wherein the base is triethylamine. Embodiment B53. The method of Embodiment B49 wherein the base is an inorganic base selected from sodium carbonate, sodium bicarbonate, sodium hydroxide, calcium hydroxide, cesium hydroxide, potassium hydroxide and potassium phosphate. Embodiment B54. The method of Embodiment B53 wherein the base is an inorganic base selected from sodium carbonate, sodium bicarbonate and sodium hydroxide. Embodiment B55. The method of Embodiment B54 wherein the base is sodium carbonate. Embodiment B56. The method of Embodiment B54 wherein the base is sodium bicarbonate. Embodiment B57. The method of any one of Embodiments B1 through B56 wherein the mole ratio of the base to a compound of Formula 3 is at least about 1. Embodiment B58. The method of B57 wherein the mole ratio of the base to a compound of Formula 3 is least about 1.5. Embodiment B59. The method of Embodiment B57 wherein the mole ratio of the base to a compound of Formula 3 is less than about 5. Embodiment B60. The method of Embodiment B57 wherein the mole ratio of the base to a compound of Formula 3 is between about 1 and 5. Embodiment B61. The method of Embodiment B57 wherein the mole ratio of the base to a compound of Formula 3 is between about 1 and 3. Embodiment B62. The method of Embodiment B57 wherein the mole ratio of the base to a compound of Formula 3 is between about 1.5 and 3. Embodiment B63. The method of any one of Embodiments B1 through B62 wherein the method is performed in a suitable solvent. Embodiment B64. The method of Embodiment B63 wherein the method is performed in a suitable solvent comprising one or more organic solvents selected from ethers, nitriles, aromatic hydrocarbons, amides, alcohols and amino-alcohols. Embodiment B65. The method of Embodiment B63 wherein the method is performed in a suitable solvent comprising one or more organic solvents selected from tetrahydrofuran, 2,5,8-trioxanonane, acetonitrile, xylenes, toluene, N,N-dimethylformamide, N,N-dimethylacetamide, methanol, ethylene glycol and N,N-dimethylethanolamine. Embodiment B66. The method of Embodiment B65 wherein the method is performed in a suitable solvent comprising ethylene glycol. Embodiment B67. The method of Embodiment B65 wherein the method is performed in a suitable solvent comprising N,N-dimethylethanolamine. Embodiment B68. The method of Embodiment B65 wherein the method is performed in a suitable solvent comprising a mixture of ethylene glycol and N,N-dimethylethanolamine. Embodiment B69. The method of Embodiment B65 wherein the method is performed in a suitable solvent consisting of ethylene glycol and N,N-dimethylethanolamine. Embodiment B70. The method of any one of Embodiments B1 through B69 wherein the method is performed at a pressure of at least about 15 psi (about 0.10 MPa) of carbon monoxide. Embodiment B71. The method of Embodiment B70 wherein the method is performed at a pressure of at least about 40 psi (about 0.27 MPa) of carbon monoxide. Embodiment B72. The method of Embodiment B71 wherein the method is performed at a pressure of at least about 70 psi (about 0.48 MPa) of carbon monoxide. Embodiment B73. The method of B72 wherein the method is performed at a pressure between about 70 and 225psi (about 0.48 to 1.5 MPa) of carbon monoxide. Embodiment B74. The method of any one of Embodiments B1 through B73 wherein the method is performed at a temperature greater than 70 °C. Embodiment B75. The method of Embodiment B74 wherein the method is performed at a temperature between about 70 °C and about 150 °C. Embodiment B76. The method of Embodiment B74 wherein the method is performed at a temperature between about 80 °C and about 120 °C. Embodiment B77. The method of Embodiment B74 wherein the method is performed at a temperature between about 100 °C and about 120 °C. Embodiment C1. The method described in the Summary for preparing a compound of Formula 6 using a compound of Formula 1 characterized by preparing a compound of Formula 1 using the method disclosed in any of Embodiments A1 through B77. Embodiment C2. The method of Embodiment C1 wherein R1is F, Cl, CN or C1–C4alkyl. Embodiment C3. The method of Embodiment C2 wherein R1is F, Cl, methyl or ethyl. Embodiment C4. The method of Embodiment C3 wherein R1is F, Cl or methyl. Embodiment C5. The method of Embodiment C4 wherein R1is Cl or methyl. Embodiment C6. The method of Embodiment C2 wherein R1is C1–C4alkyl. Embodiment C6a. The method of Embodiment C5 or Embodiment C6 wherein R1is methyl. Embodiment C7. The method of any one of Embodiments C1 through C6a wherein R2is H, F or Cl. Embodiment C8. The method Embodiment C7 wherein R2is H. Embodiment C9. The method of any one of Embodiments C1 through C8 wherein R3is chloro or cyano. Embodiment C10. The method Embodiment C9 wherein R3is chloro. Embodiment C11. The method Embodiment C9 wherein R3is cyano. Embodiment C12. The method of any one of Embodiments C1 through C11 wherein R4is H, F or Cl. Embodiment C13. The method Embodiment C12 wherein R4is H. Embodiment C14. The method Embodiment C12 wherein R4is Cl. Embodiment C15. The method Embodiment C12 wherein R4is F. Embodiment C16. The method of any one of Embodiments C1 through C13 wherein R5is H, methyl, isopropyl, cyclopropyl, cyclobutyl, cyclopropylmethyl, methylcyclopropyl or cyclopropylcyclopropyl. Embodiment C17. The method of C16 wherein R5is H, methyl, isopropyl, cyclopropyl, or cyclopropylcyclopropyl. Embodiment C18. The method of Embodiment C17 wherein R5is H, methyl, isopropyl or cyclopropylcyclopropyl. Embodiment C19. The method of Embodiment C18 wherein R5is H, methyl or isopropyl. Embodiment C20. The method of Embodiment C19 wherein R5is H. Embodiment C21. The method of Embodiment C19 wherein R5is methyl. Embodiment C22. The method of Embodiment C19 wherein R5is isopropyl. Embodiment C23. The method of any one of Embodiments C1 through C22 wherein Y1is Cl, Br or CF3. Embodiment C24. The method of Embodiment C23 wherein Y1is Br or CF3. Embodiment C25. The method of Embodiment C24 wherein Y1is CF3. Embodiment C26. The method of Embodiment C24 wherein Y1is Br. Embodiment C27. The method of any one of Embodiments C1 through C26 wherein Y2is Cl or Br. Embodiment C28. The method of Embodiment C27 wherein Y2is Br. Embodiment C29. The method of Embodiment C27 wherein Y2is Cl. Embodiment C30. The method of any one of Embodiments C1 through C29 wherein Y3is Cl. Embodiment C31. The method of any one of Embodiments C1 through C30 wherein n is 0 or 1. Embodiment C32. The method of Embodiment C31 wherein n is 0. Embodiment C33. The method of any one of Embodiments C1 through C32 wherein the compound of Formula 6 is chlorantraniliprole or cyantraniliprole. Embodiment C34. The method of any one of Embodiments C1 through C33 wherein the compound of Formula 6 is chlorantraniliprole. Embodiments of this disclosure, including Embodiments 1-C34 above as well as any other embodiments described herein, can be combined in any manner, and the descriptions of variables in the embodiments pertain not only to the compounds of Formula 1, 2 and 6 but also to the starting compounds and intermediate compounds useful for preparing the compounds of Formula 1, 2 and 6. In addition, embodiments of this disclosure, including Embodiments 1-C33 above as well as any other embodiments described herein, and any combination thereof, pertain to the methods of the present disclosure. In the following Schemes the definitions of R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, X and L in the compounds of Formula 1 through 7 below are as defined above in the Summary unless otherwise indicated. As shown in Scheme 1, this disclosure relates to a method for preparing a compound of Formula 1 catalyzed carbonylation, followed by amination. In the present method an of Formula 3 and an alcohol of Formula 4 are combined (i.e., contacted) in the presence of a palladium source, a ligand, a base and carbon monoxide to provide the corresponding aminobenzoate ester of Formula 2, which is then treated with an amine of Formula 5 to provide the corresponding aminobenzamide of Formula 1. Scheme 1 The palladium source can be either a soluble palladium compound or palladium source on an insoluble support. Examples of suitable soluble palladium compounds include palladium(II) carboxylates, such as palladium(II) acetate (i.e., Pd(OAc)2), palladium(II) trifluoroacetate, palladium(II) propionate, and palladium(II) benzoate; palladium salts of mineral acids, such as palladium(II) chloride (i.e., PdCl2), palladium(II) bromide, and palladium(II) sulfate; and other palladium complexes such as (dibenzylideneacetone)dipalladium(0) and palladium(II) acetylacetonate (i.e., Pd(acac)2), all of which are commercially available. Examples of suitable supported palladium sources include palladium on carbon and palladium (II) hydroxide on carbon. Numerous grades of unreduced and pre-reduced palladium on carbon are commercially available containing from 1 to 20 wt% palladium with different metal deposition patterns (e.g., uniform and eggshell), and utilize a variety of carbon types (e.g., peat, coconut and wood). The ligand of the present disclosure can be a bidentate phosphine such as the compound of Formula 7 as shown below in Figure 1. Figure 1 In the compound of Formula 7, L is a substituted or unsubstituted bridging group. Examples of suitable L groups include, but are not limited to, -(CH2)n-, 1,4'-ferrocene, 2,2'-diphenyl ether, 1,2-xylene and 4,5-xanthene. In a compound of Formula 7, each R7, R8, R9and R10is independently aryl or aryl. Examples of aryl groups used herein include monocyclic aromatic hydrocarbons as phenyl) and oxygen-containing aromatic heterocycles (such as furyl). Examples of substituted aryl groups as used herein include aryl groups where one or more hydrogens of the aryl group have been replaced by an alkyl, alkoxy, chlorine, fluorine or fluoromethyl group (e.g. tolyl, and xylyl). Ligands of particular note in the present disclosure include 1,4-bis(diphenylphosphino)butane (dppb), 1,1'-bis(diphenylphosphino)ferrocene (dppf), and 9,9-dimethyl-4,5-bis(diphenylphosphino)- xanthene (Xantphos). In the context of the present disclosure the palladium source is most often combined with the ligand (i.e., compound of Formula 7) at the start of the carbonylation reaction. The palladium source and ligand, however, may also be provided in the form of a pre-formed complex (i.e., of palladium source and ligand). Examples of pre-formed complexes useful in the present disclosure include the commercially available [1,1’-bis(diphenylphosphino)- ferrocene]palladium(II) dichloride and (9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene)- palladium(II) dichloride. Catalyst loadings that are less than 0.1 mol% may be achieved with a single use of a soluble palladium source as the catalyst. Typically, with a soluble palladium source, the palladium to ligand molar ratio is from about 1:0.5 to 1:100. A ratio between 1:10 and 1:5 provides the quickest carbon monoxide uptake resulting in reduced reaction times. Use of a soluble palladium source and ligand to form a highly active catalyst system is exemplified by the combination of palladium (II) acetate and the ligand 1,1'-bis(diphenylphosphino)ferrocene (dppf). As demonstrated in Step A of present Examples 1 and 2, and Experiment 10 of Example 3, complete conversion of the starting material may be consistently attained with 0.01 mol% palladium (II) acetate and 0.10 mol% dppf (i.e., a palladium to ligand ratio of 1:10) after a period of 7-8 hours at 120 °C under a carbon monoxide pressure of 75 psig (0.52 MPa). Selectivity for the desired product was 94.7 to 96.7 Area% by HPLC. Alternatively, due to the insolubility of the support material in the reaction mass, catalyst loadings that are less than 0.1 mol% may also be achieved through recycling of a supported palladium source as the catalyst. Typically, with a supported palladium source, the palladium to ligand molar ratio is from about 1:1 to 1:5 in the first run using fresh a supported palladium source and then about 1:0.5 to 1:5 in subsequent runs using the recycled palladium source. Use of a supported palladium source and ligand is exemplified by palladium on carbon (e.g., Johnson Matthey 10R39) combined with the ligand 1,1'-bis(diphenylphosphino)ferrocene (dppf). As demonstrated in Step A of Example 6, complete conversion of the starting material was attained with 0.10 mol% of fresh palladium on carbon and 0.50 mol% dppf (i.e., a palladium to ligand ratio of 1:5) after a period of about 4 hours at 120 °C. The palladium on carbon (i.e., supported palladium source) was recovered from the reaction mass by a combination of decantation and filtration. The recovered material was recycled in Experiment A of Example 7 to which 0.50 mol% dppf added. Under the same reaction conditions, conversion was complete after about 6 A second recycle was carried out in the same manner (see Experiment B of Example 7) resulting in complete conversion after about 7 hours. Selectivity for the desired product ranged from 96.3-97.0 Area% by HPLC. Given that one charge of palladium on carbon was used for all three runs, the effective catalyst loading was 0.033 mol% (i.e., 0.1 mol% divided by 3 runs). The carbonylation reaction of Scheme 1 produces HX (wherein X is Br or I) as a by- product, which is neutralized by addition of a base. In general, any base compatible with the reaction mixture and process conditions may be employed. Organic bases such as tertiary amines (e.g., triethylamine or tributylamine) are particularly suitable. Inorganic bases such as sodium carbonate or sodium bicarbonate; and hydroxides of sodium, calcium, cesium and potassium may also be used. At least 1 molar equivalent of base versus compound of Formula 3 is required by stoichiometry. Reliable high conversions of the compounds of Formula 3 to the compounds of Formula 2 were typically achieved with 1.5 to 3.0 molar equivalents of base relative to the compound of Formula 3. Although higher levels of base can be used there is no particular advantage in doing so and higher levels increase raw material and waste processing costs. The process of Scheme 1 is typically conducted in a suitable organic solvent. Examples of suitable organic solvents include ethers, such as tetrahydrofuran and 2,5,8-trioxanonane (diglyme); nitriles, such as acetonitrile; aromatic hydrocarbons, such as xylenes and toluene; amides, such as N,N-dimethylformamide and N,N-dimethylacetamide; and mixtures thereof. Alcohols of Formula 4 may serve as both the reactant in the carbonylation reaction and the solvent for the process. Examples include alcohols, such as methanol, ethanol and ethylene glycol; and amino-alcohols, such as N,N-dimethylethanolamine; and mixtures thereof. Bifunctional solvents, such as ethylene glycol and N,N-dimethylethanolamine, either alone or in combination, are particularly advantageous in improving the rate and selectivity of the amination reaction. Phosphine ligands are sensitive to the presence of oxygen in the process of Scheme 1. As a result, the process is preferentially carried out under substantially oxygen free conditions to maintain catalyst activity and prevent formation of unwanted by-products. Standard techniques that can be used to remove oxygen include purging the reactor system and / or sparging the starting material solution with an inert gas, such as nitrogen or argon. The presence of water may also lead to degradation of certain phosphine ligands and formation of by-products. Hence, solvents used in the process should be substantially water free. Standard solvent drying techniques that may be used include azeotropic distillation or drying agents such as molecular sieves, potassium carbonate and magnesium sulfate. Process conditions, such as temperature and carbon monoxide pressure, and the catalyst system consisting of a palladium source and a ligand, are selected to achieve high catalyst activity and product selectivity. The activity” in the context of the present disclosure refers to the required catalyst expressed in mol% versus the starting material (i.e., compound of Formula 3), that results in complete or near complete consumption (i.e., 98% or greater) of the starting material in an acceptable period of time (i.e., 18 h or less). The carbonylation reaction is typically conducted between about 70 °C and 150 °C, and preferably between about 100 °C to 120 °C for complete or near complete conversion of the starting material in a commercially acceptable period of time while maintaining a high selectivity. Catalyst loadings that are less than 0.1 mol% are utilized in the present disclosure at carbon monoxide pressures of 70 psig (0.48 MPa) or greater for complete or near complete conversion of the starting material in a commercially acceptable period of time while maintaining a high selectivity. Typically, pressures between about 70 and 225 psig (0.48 to 1.5 MPa) are generally preferred in order to utilize standard, multipurpose, commercial equipment. In the present disclosure, carbon monoxide pressures greater than 70 psig (0.48 MPa) and properly selected catalyst-ligand combinations with low palladium catalyst loadings (i.e., 0.05 mol% or less) result in near to complete conversion of the starting material within 16 h or less. The reaction mass produced from the carbonylation reaction may be used in the subsequent amination stage of the process without the need to isolate the carbonylated product (i.e., the compound of Formula 2). Typically, when a soluble palladium source is used in the carbonylation step of Scheme 1, the entire reaction mass obtained can be used in the subsequent amination reaction. Alternatively, when using a supported palladium source, the supported palladium source is removed from the reaction mass by techniques well known to those skilled in the art, such as decantation or filtration. As discussed above, recovered supported palladium may be recycled to subsequent carbonylation reactions in place of fresh material. Optionally, by-products, such as the base-HX salt formed in the carbonylation reaction, may be removed from the reaction mass by standard techniques well known to those, such as extraction. Furthermore, the carbonylated product may be isolated and purified from the reaction by standard techniques well known to those skilled in the art, such as crystallization and filtration. In the second step of Scheme 1, an amination reaction is typically carried out by contacting the reaction mass containing an ester compound of Formula 2 produced from the carbonylation reaction with an amine of Formula 5. The amine of Formula 5 may be added as a pure material or as a solution in a suitable solvent as previously described for the carbonylation reaction. The solvent may be the same or different from that used for the carbonylation reaction. The amination reaction is typically conducted at temperatures between 70 °C and 150 °C. Temperatures between 80 °C and 120 °C are especially preferred, since they provide complete or near complete consumption 98% or greater) in an acceptable period of time (i.e., 18 h or less) while maintaining high for the desired product (i.e., compound of Formula 1). While only one molar equivalent of amine versus the compound of Formula 2 is required by stoichiometry, typically, complete or near complete consumption of the compound of Formula 2 within 18 h or less is achieved using 5 to 10 molar equivalents within the temperature range of 80 °C and 120 °C. The product of the amination reaction (i.e., compound of Formula 1) may be isolated from the reaction mass by standard techniques well known to those skilled in the art. Since compounds of Formula 1 are typically solids at ambient temperature, they frequently crystallize from the reaction mass and are most easily isolated by filtration, optionally followed by washing with water and / or an organic solvent and drying. Addition of an “anti- solvent” may be useful to reduce the solubility of the product. For example, if the process is conducted in a water miscible organic solvent, such as acetonitrile, methanol or ethylene glycol, then addition of water typically increases the yield of crystallized product. The present method provides an efficient means to produce aminobenzamides of Formula 1 from anilines of Formula 3. The compounds of Formula 3 are generally known in the art and are commercially available or can be prepared from literature procedures. For example, a compound of Formula 3 wherein R1is CH3, R2is Cl and X is Br can be prepared as found in PCT Patent Publication WO 2008 / 051533 on page 93. A compound of Formula 3 wherein R1is CH3, R2is cyano and X is Br can be prepared as found in PCT Patent Publication WO 2010 / 093191 on pages 83 and 84. Without further elaboration, it is believed that one skilled in the art using the preceding description can utilize the present disclosure to its fullest extent. The following examples are, therefore, to be construed as merely illustrative and not limiting of the disclosure in any way whatsoever. Ambient or room temperature is defined as about 20–25 °C. Pressure is defined as the pressure measured relative to the ambient atmospheric pressure. The term “psig” means gauge pressure in pounds per square inch (i.e., pounds per square inch gauge). “MPa” means megapascal. Percentages are by weight (i.e., wt%) except where otherwise indicated. The term HPLC means high performance liquid chromatography. HPLC Area% reports the area of an HPLC chromatogram peak as a percentage of the total area of all chromatogram peaks. In the following Examples and Tables “Exp.” stands for experiment, and “eq.” stands for mole equivalents. All patents and publications cited herein are fully incorporated by reference in their entirety. 1 Preparation of 2-amino-5-chloro-N,3-dimethylbenzamide (Compound 1a) using palladium (II) acetate and 1,1’-bis(diphenylphosphino)ferrocene. Step A: Preparation of 2-hydroxyethyl 2-amino-5-chloro-3-methylbenzoate (Compound 2a). A 600 mL Parr pressure reactor fitted with an overhead stirrer, a thermocouple, a pressure transducer and a gas inlet was charged with a solution of palladium (II) acetate (4.5 mg, 0.020 mmol, 0.010 mol%) and 1,1’-bis(diphenylphosphino)ferrocene (DPPF) (111 mg, 0.200 mmol, 0.100 mol%) in dichloromethane (2 mL). A stream of nitrogen was passed over the solution, evaporating the solvent and leaving the catalyst residue in the bottom of the reactor. To the reactor was added a solution of 2-bromo-4-chloro-6- methylbenzeneamine (44.0 g, 200 mmol) and triethylamine (61.0 g, 603 mmol, 3.02 eq.) in ethylene glycol (204 g). The reactor was sealed and purged five times by pressurizing to 45 psig (0.31 MPa) with nitrogen followed by venting. The reactor was agitated (900 rpm), and purged five additional times by pressurizing to 45 psig (0.31 MPa) with nitrogen followed by venting. The reactor was pressurized with carbon monoxide (75 psig) (0.52 MPa), heated to 120 °C and agitated under these conditions for 18 h. The observed carbon monoxide uptake ceased within 8 h of carbon monoxide pressurization. The reactor was cooled to ambient temperature, vented, purged with nitrogen (45 psig) (0.31 MPa) and vented. HPLC analysis of the resultant reaction mass showed 96.7 Area% of Compound 2a and no detectible starting material. Step B: Preparation of 2-amino-5-chloro-N,3-dimethylbenzamide (Compound 1a) at 80 °C. A 300 mL Parr pressure reactor fitted with an overhead stirrer, a thermocouple, a pressure transducer and a gas inlet was charged with a portion of the reaction mass from Example 1 Step A (141 g, containing approximately 91.3 mmol of Compound 2a) and methylamine (35% solution in ethylene glycol, 40.5 g, 456 mmol, 5.0 eq.). The reactor was sealed and purged five times by pressurizing to 45 psig (0.31 MPa) with nitrogen followed by venting. The reactor was pressurized with methylamine gas (15-30 psig) (0.10-0.21 MPa). The reactor was agitated (500 rpm) and heated at 80 °C for 18 h. The reactor was cooled to ambient temperature. HPLC analysis of the resultant reaction mass showed 94.1 Area% of Compound 1a and 1.3 Area% of Compound 2a. The reaction mass was transferred to a 500 ml, glass bottle equipped with a magnetic stirrer. To the reaction mass was added water (2.0 volumes versus the reaction mass), stirred for 1 h and filtered. The filtered material was washed with water (60 mL) and dried in a vacuum oven at 60 °C to yield a solid (15.7 g) containing the title compound (referred to as the isolated product). The isolated product was characterized by1H NMR.1H NMR purity of the isolated product: 97.5 wt%. Overall yield of the isolated product beginning from 2-bromo-4-chloro-6- methylbenzeneamine: 84%. EXAMPLE 2 Preparation 2-amino-5-chloro-N,3-dimethylbenzamide (Compound 1a) using palladium (II) acetate and 1,1’-bis(diphenylphosphino)ferrocene. Step A: Preparation of 2-hydroxyethyl 2-amino-5-chloro-3-methylbenzoate (Compound 2a) A 600 mL Parr pressure reactor fitted with an overhead stirrer, a thermocouple, a pressure transducer and a gas inlet was charged with a solution of palladium (II) acetate (4.5 mg, 0.020 mmol, 0.010 mol%) and 1,1’-bis(diphenylphosphino)ferrocene (DPPF) (111 mg, 0.200 mmol, 0.100 mol%) in dichloromethane (2 mL). A stream of nitrogen was passed over the solution, evaporating the solvent and leaving the catalyst residue in the bottom of the reactor. To the reactor was added a solution of 2-bromo-4-chloro-6- methylbenzeneamine (44.0 g, 200 mmol) and triethylamine (61.0 g, 603 mmol, 3.02 eq.) in ethylene glycol (204 g). The reactor was sealed and purged five times by pressurizing to 45 psig (0.31 MPa) with nitrogen followed by venting. The reactor was agitated (900 rpm), and purged five additional times by pressurizing to 45 psig (0.31 MPa) with nitrogen followed by venting. The reactor was pressurized with carbon monoxide (75 psig) (0.52 MPa), heated to 120 °C and agitated under these conditions for 18 h. The observed carbon monoxide uptake ceased within 8 h of carbon monoxide pressurization. The reactor was cooled to ambient temperature, vented, purged with nitrogen (45 psig) (0.31 MPa) and vented. HPLC analysis of the resultant reaction mass showed 95.6 Area% of Compound 2a and no detectible starting material. Step B: Preparation of 2-amino-5-chloro-N,3-dimethylbenzamide (Compound 1a) at 80 °C for 3 h, and then at 100 °C. A 300 mL Parr pressure reactor fitted with an overhead stirrer, a thermocouple, a pressure transducer and a gas inlet was charged with a portion of the reaction mass from Example 1 Step A (141 g, containing approximately 91.3 mmol of Compound 2a) and methylamine (35% solution in ethylene glycol, 40.5 g, 456 mmol, 5.0 eq.). The reactor was sealed and purged five times by pressurizing to 45 psig (0.31 MPa) with nitrogen followed by venting. The reactor was pressurized with methylamine gas (15-30 psig) (0.10-0.21 MPa). The reactor was agitated (500 rpm), heated at 80 °C for 3 h, and then heated at 100 °C for 20 h. The reactor was cooled to ambient HPLC analysis of the resultant reaction mass showed 93.8 Area% of Compound no detectible Compound 2a. The reaction mass was transferred to a 500 ml, glass bottle equipped with a magnetic stirrer. To the reaction mass was added water (1.7 volumes versus the reaction mass), stirred for 1 h and filtered. The filtered material was washed with water (60 mL) and dried in a vacuum oven at 60 °C to yield a solid (15.1 g) containing the title compound (Compound 1a) (referred to as the isolated product). The isolated product was characterized by quantitative1H NMR.1H NMR purity of the isolated product: 99.9 wt%. Overall yield of the isolated product beginning from 2-bromo-4-chloro-6- methylbenzeneamine: 83%. EXAMPLE 3 Preparation of 2-hydroxyethyl 2-amino-5-chloro-3-methylbenzoate (Compound 2a) using different ratios of palladium (II) acetate and 1,1’-bis(diphenylphosphino)- ferrocene. 2-Hydroxyethyl 2-amino-5-chloro-3-methylbenzoate was prepared in Experiments 1-10 using the parameters in Table A below. Experiments 1-10 were conducted using a Biotage Endeavor pressure reactor system (8 x 8 mL). For each experiment a reaction vial was charged with the amount of 1,1’-bis(diphenylphosphino)ferrocene (DPPF) specified in Table A (11-2.2 mg, 0.020-0.0040 mmol) as a 110 mg / mL solution in dichloromethane (100-20 µL). A stream of nitrogen was passed over the solution to evaporate the solvent. The reaction vial was then charged with the amount of palladium(II) acetate (Pd(OAc)2) specified in Table A (0.90-0.090 mg, 0.0040-0.00040 mmol) as a 10 mg / mL solution in dichloromethane (90- 9.0 µL). A stream of nitrogen was passed over the solution to evaporate the solvent. To the residue in each vial was added a solution of 2-bromo-4-chloro-6- methylbenzeneamine (0.882 g, 4.00 mmol) and triethylamine (1.21 g, 12.0 mmol) in ethylene glycol (4.48 g). The reactor was sealed and purged three times by pressurizing to 30-45 psig (0.21-0.31 MPa) with nitrogen followed by venting. The reaction mixture was agitated (600 rpm). The reactor was pressurized with carbon monoxide (75 psig) (0.52 MPa), heated to 120 °C, and agitated for 16 h. The time required to attain full consumption of the starting material was based upon the observed cessation of carbon monoxide uptake. The reactor was cooled to ambient temperature and vented. A sample of the reaction mass was analyzed by HPLC. Results are given in Table A. A Summary of Reaction Parameters held constant: 3.0 eq. Et3N; 75 psig (0.52 MPa) CO; 600 rpm; 120 °C; 16 h. Ratio of Pd(OAc)Experiment2DPPF Charge Palladium Time Starting Material Compound 2a : me requ re o reac compe e consump on o e s ar ng ma er a ase upon cessa on o car on monoxide uptake. iii: Residual 2-bromo-4-chloro-6-methyl-benzeneamine in final reaction mass by HPLC. iv: Compound 2a in final reaction mass by HPLC. EXAMPLE 4 Preparation of 2-hydroxyethyl 2-amino-5-chloro-3-methylbenzoate (Compound 2a) using [1,1’-bis(diphenylphosphino)ferrocene]palladium(II) dichloride in various ratios with 1,1’-bis(diphenylphosphino)ferrocene. . 2-Hydroxyethyl 2-amino-5-chloro-3-methylbenzoate was prepared in Experiments 11- 14 using the parameters in Table B below. Experiments 11-14 were conducted using a Biotage Endeavor pressure reactor system (8 x 8 mL). For each experiment a reaction vial was charged with the amount of 1,1’-bis(diphenylphosphino)ferrocene (DPPF) specified in Table B (11-5.5 mg, 0.020-0.010 mmol) as a 110 mg / mL solution in dichloromethane (100-50 µL). A stream of nitrogen was passed over the solution to evaporate the solvent. To the residue was added [1,1’-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (PdCl2(dppf)) (0.29 mg, 0.00040 mmol), followed by a solution of 2-bromo-4-chloro-6-methylbenzeneamine (0.882 g, 4.00 mmol) and triethylamine (1.21 g, 12.0 mmol) in ethylene glycol (4.48 g). The reactor was sealed and purged three times by pressurizing to 30-45 psig (0.21-0.31 MPa) with nitrogen followed by venting. The reaction mixture was agitated (600 rpm). The reactor was pressurized with carbon monoxide (75 psig) (0.52 MPa), heated to 120 °C, and agitated for 16 h. The time required to attain full of the starting material was based upon the observed cessation of carbon monoxide The reactor was cooled to ambient temperature and vented. A sample of the reaction mass was analyzed by HPLC. Results are given in Table B. Table B Summary of Reaction Parameters held constant: 3.0 eq. Et3N; 75 psig (0.52 MPa) CO; 600 rpm; 120 °C; 16 h. Ratio of PdCl (dppf)Experiment2DPPF Charge palladium to Time Starting Material Compound 2a : c u es e2pp co p e as e as e c a ge o e eac o .iii: Time required to reach complete consumption of the starting material based upon cessation of carbon monoxide uptake. iv: Residual 2-bromo-4-chloro-6-methyl-benzeneamine in final reaction mass by HPLC. v: Compound 2a in final reaction mass by HPLC. EXAMPLE 5 Preparation of 2-hydroxyethyl 2-amino-5-chloro-3-methylbenzoate (Compound 2a) using a 1:1 ratio of palladium (II) acetate to 1,1’-bis(diphenylphosphino)ferrocene at different temperatures, pressures and amounts of base. 2-Hydroxyethyl 2-amino-5-chloro-3-methylbenzoate was prepared in Experiments 15- 22 using the parameters in Table C below. Experiments 15-22 were conducted using a Biotage Endeavor pressure reactor system (8 x 8 mL). For each experiment a reaction vial was charged with a 110 mg / mL solution of 1,1’-bis(diphenylphosphino)ferrocene (DPPF) (11 mg, 0.020 mmol) in dichloromethane (100 µL). A stream of nitrogen was passed over the solution to evaporate the solvent. The reaction vial was then charged with a 10 mg / mL solution of palladium(II) acetate (0.90 mg, 0.0040 mmol) in dichloromethane (90 µL). A stream of nitrogen was passed over the solution to evaporate the solvent. To the residue was added a solution of 2-bromo-4-chloro-6-methylbenzeneamine (0.882 g, 4.00 mmol) and an amount of triethylamine specified in Table C (0.607-1.21 g, 6.00-12.0 mmol) in ethylene glycol (4.12 g). The reactor was sealed and purged three times by pressurizing to 30-45 psig (0.21-0.31 MPa) with nitrogen followed by venting. The reaction mixture was agitated (600 rpm), pressurized with carbon monoxide (30-75 psig) (0.21- 0.52 MPa) and heated (100-120 °C), for 16 The time required to attain full consumption of the starting material was based upon the cessation of carbon monoxide uptake. The reactor was cooled to ambient temperature and vented. A sample of the reaction mass was analyzed by HPLC. Results are given in Table C. Table C Summary of Reaction Parameters held constant: Pd:Ligand ratio 1:1; 600 rpm; 16 h. Pd(OAc)2DPPFEt3NReactio CO 100% Starting Compound 2a Exp. No. Charge Charge Charge n Temp. Pressure Conv. Material ii: Time required to reach complete consumption of the starting material based upon cessation of carbon monoxide uptake. iii: Residual 2-bromo-4-chloro-6-methyl-benzeneamine in final reaction mass by HPLC. iv: Compound 2a in final reaction mass by HPLC. v: 0.21 MPa. vi: 0.52 MPa. EXAMPLE 6 Preparation of 2-amino-5-chloro-N,3-dimethylbenzamide using 10% palladium on carbon and 1,1’-bis(diphenylphosphino)ferrocene. Step A: Preparation of 2-hydroxyethyl 2-amino-5-chloro-3-methylbenzoate (Compound 2a). A 600 mL Parr pressure reactor fitted with an overhead stirrer, a thermocouple, a pressure transducer and a gas inlet was charged with 2-bromo-4-chloro-6- methylbenzeneamine (44.0 g, 200 mmol), ethylene glycol (204 g) and triethylamine (61.0 g, 603 mmol, 3.02 eq.). The reaction mixture was treated with 1,1’-bis(diphenyl- phosphino)ferrocene (DPPF) (0.554 g, 1.00 mmol, 0.50 mol%) followed by 10% palladium on carbon (Johnson Matthey; Type 10R39; 59.9% water-wet) (0.530 g, 0.200 mmol Pd, 0.10 mol%). The reactor was sealed and purged five times by pressurizing to 45 psig (0.31 MPa) with nitrogen followed by venting. The was agitated (900 rpm), and purged three additional times by pressurizing to 45 psig MPa) with nitrogen followed by venting. The reactor was pressurized with carbon monoxide (75 psig) (0.52 MPa), heated to 100 °C and agitated under these conditions for 18 h. The observed carbon monoxide uptake ceased within 4 h of carbon monoxide pressurization. The reactor was vented. The reaction mass was stirred an additional 3 h at 100 °C. Reactor agitation was stopped, and the undisturbed reaction mass was allowed to cool to room temperature overnight. The supernatant liquid was decanted, leaving the catalyst residue in the reactor. The decanted liquid was passed through filter paper to remove suspended catalyst residue. HPLC analysis of the filtrate (referred to as the clarified reaction mass) showed 96.3 Area% of Compound 2a and no detectible starting material. Step B: Preparation of 2-amino-5-chloro-N,3-dimethylbenzamide (Compound 1a). A 300 mL Parr pressure reactor fitted with an overhead stirrer, a thermocouple, a pressure transducer and a gas inlet was charged with a portion of the reaction mass from Example 1 Step A (141 g, containing approximately 91.3 mmol of Compound 2a) and methylamine (35% solution in ethylene glycol, 40.5 g, 456 mmol, 5.0 eq.). The reactor was sealed and purged five times by pressurizing to 45 psig (0.31 MPa) with nitrogen followed by venting. The reactor was pressurized with methylamine gas (15-30 psig) (0.10-0.21 MPa). The reactor was agitated (500 rpm) and heated at 80 °C for 18 h. The reactor was cooled to ambient temperature. HPLC analysis of the resultant reaction mass showed 91.7 Area% of Compound 1a and 1.8 Area% of Compound 2a. The reaction mass was transferred to a 500 ml, glass bottle equipped with a magnetic stirrer. To the reaction mass was added water (2.0 volumes versus the reaction mass), stirred for 1 h and filtered. The filtered material was washed with water (60 mL) and dried in a vacuum oven at 60 °C to yield a solid (15.8 g) containing the title compound (Compound 1a) (referred to as the isolated product). The isolated product was characterized by quantitative1H NMR.1H NMR purity of the isolated product: 97.4 wt%. Overall yield of the isolated product beginning from 2-bromo-4-chloro-6- methylbenzeneamine: 85%. EXAMPLE 7 Preparation of 2-hydroxyethyl 2-amino-5-chloro-3-methylbenzoate (Compound 2a) with catalyst recycling. Experiment A: Catalyst Recycle #1. The 600 mL Parr pressure reactor containing the catalyst residue from Example 6 Step A was charged with 2-bromo-4-chloro-6-methylbenzeneamine (44.0 g, 200 mmol), ethylene glycol (204 g) and triethylamine (61.0 g, 603 mmol, 3.02 eq.). A portion of the ethylene glycol was used to wash the filtered catalyst residue from the filter paper that had been used to clarify the reaction mass of Example 6 Step The reaction mixture was treated with 1,1’- bis(diphenylphosphino)ferrocene (DPPF) g, 1.00 mmol, 0.50 mol%). The reactor was sealed and purged five times by pressurizing to 45 psig (0.31 MPa) with nitrogen followed by venting. The reactor was agitated (900 rpm), and purged three additional times by pressurizing to 45 psig (0.31 MPa) with nitrogen followed by venting. The reactor was pressurized with carbon monoxide (75 psig) (0.52 MPa), heated to 100 °C and agitated under these conditions for 66 h. The observed carbon monoxide uptake ceased within 6 h of carbon monoxide pressurization. The reactor was vented. The reaction mass was stirred an additional 3 h at 100 °C. Reactor agitation was stopped. The undisturbed reaction mass was allowed to cool to room temperature overnight. The supernatant liquid was decanted, leaving the catalyst residue in the reactor. The decanted liquid was passed through filter paper to remove suspended catalyst residue. HPLC analysis of the filtrate (referred to as the clarified reaction mass) showed 96.9 Area% of Compound 2a and no detectible starting material. Experiment B: Catalyst Recycle #2. To the 600 mL Parr pressure reactor containing the catalyst residue from Example 7 Experiment A was charged 2-bromo-4-chloro-6-methylbenzeneamine (44.0 g, 200 mmol), ethylene glycol (204 g) and triethylamine (61.0 g, 603 mmol, 3.02 eq.). A portion of the ethylene glycol was used to wash the filtered catalyst residue from the filter paper that had been used to clarify the reaction mass of Example 7 Experiment A. The reaction mixture was treated with 1,1’-bis(diphenylphosphino)ferrocene (DPPF) (0.554 g, 1.00 mmol, 0.50 mol%). The reactor was sealed and purged five times by pressurizing to 45 psig (0.31 MPa) with nitrogen followed by venting. The reactor was agitated (900 rpm), and purged three additional times by pressurizing to 45 psig (0.31 MPa) with nitrogen followed by venting. The reactor was pressurized with carbon monoxide (75 psig) (0.52 MPa), heated to 100 °C and agitated under these conditions for 18 h. The observed carbon monoxide uptake ceased within 7 h of carbon monoxide pressurization. The reactor was vented. The reaction mass was stirred an additional 3 h at 100 °C. Reactor agitation was stopped. The undisturbed reaction mass was allowed to cool to room temperature overnight. The supernatant liquid was decanted, leaving the catalyst residue in the reactor. The decanted liquid was passed through filter paper to remove suspended catalyst residue. HPLC analysis of the filtrate (referred to as the clarified reaction mass) showed 97.0 Area% of Compound 2a and no detectible starting material. Experiment C: Catalyst Recycle #3. To the 600 mL Parr pressure reactor containing the catalyst residue from Example 7 Experiment B was charged 2-bromo-4-chloro-6-methylbenzeneamine (44.0 g, 200 mmol), ethylene glycol (204 g) and triethylamine (61.0 g, 603 mmol, 3.02 eq.). A portion of the ethylene glycol was used to wash the catalyst residue from the filter paper that had been used to clarify the reaction mass of 7 Experiment B. The reaction mixture was treated with 1,1’-bis(diphenylphosphino)ferrocene (DPPF) (0.554 g, 1.00 mmol, 0.50 mol%). The reactor was sealed and purged five times by pressurizing to 45 psig (0.31 MPa) with nitrogen followed by venting. The reactor was agitated (900 rpm), and purged three additional times by pressurizing to 45 psig (0.31 MPa) with nitrogen followed by venting. The reactor was pressurized with carbon monoxide (75 psig) (0.52 MPa), heated to 100 °C and agitated under these conditions for 264 h. The observed carbon monoxide uptake ceased within 35 h of carbon monoxide pressurization. The reactor was vented. The reaction mass was stirred an additional 3 h at 100 °C. Reactor agitation was stopped. The undisturbed reaction mass was allowed to cool to room temperature overnight. The supernatant liquid was decanted, leaving the catalyst residue in the reactor. The decanted liquid was passed through filter paper to remove suspended catalyst residue. HPLC analysis of the filtrate (referred to as the clarified reaction mass) showed 97.8 Area% of Compound 2a and no detectible starting material. EXAMPLE 8 Preparation of 2-hydroxyethyl 2-amino-5-chloro-3-methylbenzoate (Compound 2a) using 5% Palladium on Carbon with various ligands and Pd to Ligand ratios. 2-Hydroxyethyl 2-amino-5-chloro-3-methylbenzoate was prepared in Experiments 23- 38 using the parameters in Table D below. Experiments 23-38 were conducted using a Biotage Endeavor pressure reactor system (8 x 8 mL). For each experiment a reaction vial was charged with the amount of 5% palladium on carbon (Johnson Matthey; Type 5R39; 59.5% water-wet) specified in Table D (13.2-26.3 mg, 0.0025-0.0050 mmol) followed by an amount specified in Table D (0.00125-0.00500 mmol) of one of the following ligands: 1,1’-bis(diphenylphosphino)propane (DPPP) (0.52-2.06 mg); 1,1’-bis(diphenylphosphino)- butane (DPPB) (0.53-2.13 mg); 1,1’-bis(diphenylphosphino)ferrocene (DPPF) (0.69- 2.77 mg); or 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos) (0.72-2.89 mg). To the reaction vial was then added a solution of 2-bromo-4-chloro-6- methylbenzeneamine (0.110 g, 0.500 mmol) and triethylamine (0.152 g, 1.50 mmol, 3.00 eq.) in ethylene glycol (1.0 mL). The reactor was sealed and purged three times by pressurizing to 30-45 psig (0.21-0.31 MPa) with nitrogen followed by venting. The reaction mixture was agitated (300 rpm), pressurized with carbon monoxide (30 psig) (0.21 MPa), and heated (100 °C) for 4 h. The reactor was cooled to ambient temperature and vented. A sample of the reaction mass was analyzed by HPLC. Results are given in Table D. D Summary of Reaction Parameters held constant: 3.0 eq. Et3N; 30 psig (0.21 MPa) CO; 300 rpm; 100 °C; 4 h. Pd / Ligand Starting 5% Pd on Carbon Ligand / Charge Compound 2a Exp. No. Ratio Material ii: Residual 2-bromo-4-chloro-6-methyl-benzeneamine in final reaction mass by HPLC. iii: Compound 2a in final reaction mass by HPLC. EXAMPLE 9 Preparation of 2-hydroxyethyl 2-amino-5-chloro-3-methylbenzoate (Compound 2a) using different grades of Palladium on Carbon. 2-Hydroxyethyl 2-amino-5-chloro-3-methylbenzoate was prepared in Experiments 39- 50 using the parameters in Table E below. Experiments 39-50 were conducted using a Biotage Endeavor pressure reactor system (8 x 8 mL). For each experiment a reaction vial was charged with an amount of palladium on carbon specified in Table E (0.50 mol%; catalyst type given in Table E) and 1,1’-bis(diphenylphosphino)ferrocene (DPPF) (2.77 mg, 0.0050 mmol, 0.50 mol%), followed by the addition of a solution of 2-bromo-4-chloro-6-methylbenzeneamine (0.220 g, 1.00 mmol) and triethylamine (0.304 g, 3.00 mmol, 3.00 eq.) in ethylene glycol (1.73 g). The reactor was sealed and purged three times by pressurizing to 30-45 psig (0.21- 0.31 MPa) with nitrogen followed by venting. The reaction mixture was agitated (300 rpm), pressurized with carbon monoxide (30 psig) (0.21 MPa), and heated (100 °C) for 4 h. The reactor was cooled to ambient vented. A sample of the reaction mass was analyzed by HPLC. Results are given in E. Table E Summary of Reaction Parameters held constant: 3.0 eq. Et3N; 30 psig (0.21 MPa) CO; 300 rpm; 100 °C; 4 h. Pd on Pd on Carbon DPPF Pd:Ligand Starting Compound 2a Exp. No. Carbon Charge Charge Ratio Material palladium. ii: Versus 2-bromo-4-chloro-6-methylbenzeneamine starting material. iii: Residual 2-bromo-4-chloro-6-methyl-benzeneamine in final reaction mass by HPLC. iv: Compound 2a in final reaction mass by HPLC. EXAMPLE 10 Preparation of 2-hydroxyethyl 2-amino-5-chloro-3-methylbenzoate (Compound 2a) using different palladium catalysts and bases. 2-Hydroxyethyl 2-amino-5-chloro-3-methylbenzoate was prepared in Experiments 51- 55 using the parameters in Table F below. Experiments 51-55 were conducted using a Biotage Endeavor pressure reactor system (8 x 8 mL). For each experiment a reaction vial was charged with an amount of a palladium source specified in Table F (0.0050 mmol, 1.0 mol%), 1,1’- bis(diphenylphosphino)propane (DPPP) (2.06 mg, 0.0050 mmol, 1.0 mol%), and ethylene glycol (0.4 mL), followed by the addition of 2-bromo-4-chloro-6-methylbenzeneamine (0.110 g, 0.500 mmol) and an amount of the base specified in Table F in ethylene glycol (0.6 mL). The reactor was sealed and purged three times by pressurizing to 30-45 psig (0.21-0.31 MPa) with nitrogen followed by venting. The reaction mixture was agitated (300 rpm), pressurized with carbon monoxide (30 psig) (0.21 MPa), and heated (100 °C) for 4 h. The reactor was cooled to ambient temperature and sample of the reaction mass was analyzed by HPLC. Results are given in Table F. Table F Summary of Reaction Parameters held constant: Pd:Ligand ratio 1:1; 30 psig (0.21 MPa) CO; 300 rpm; 100 °C; 4 h. DPPP Starting Acid By- Pd Source / Charge Base / Charge Compound 2a Exp. No. Charge Material product iv - - - - - y- y . iii: Compound 2a in final reaction mass by HPLC. iv: By-product 2-amino-5-chloro-3-methylbenzoic acid in final reaction mass by HPLC. v: Grade of palladium on carbon supplied by Johnson Matthey (5 wt% palladium). vi: Since potassium phosphate is tribasic, 1.0 molar equivalent supplies 3.0 equivalents of base. EXAMPLE 11 Preparation of 2-hydroxyethyl 2-amino-5-chloro-3-methylbenzoate (Compound 2a) using different carbon monoxide pressures. 2-Hydroxyethyl 2-amino-5-chloro-3-methylbenzoate was prepared in Experiments 56- 61 using the parameters in Table G below. Experiments 56-61 were conducted using a Biotage Endeavor pressure reactor system (8 x 8 mL). For each experiment a reaction vial was charged with 5% palladium on carbon (Johnson Matthey, Type 5R490, 55.5% water-wet) (23.9 mg, 0.0050 mmol, 0.50 mol%) and 1,1’-bis(diphenylphosphino)ferrocene (DPPF) (2.77 mg, 0.0050 mmol, 0.50 mol%) either as a pure material or as a solution in p-dioxane (2 mL) (see Table G), followed by a solution of 2-bromo-4-chloro-6-methylbenzeneamine (0.220 g, 1.00 mmol) and triethylamine (0.304 g, 3.00 mmol, 3.00 eq.) in ethylene glycol (1.73 g). The reactor was sealed and purged three times by pressurizing to 30-45 psig (0.21-31 MPa) with nitrogen followed by venting. The reaction mixture was agitated (600 rpm), pressurized with carbon monoxide (5, 15 or 30 psig) (0.034, 0.10 or 0.21 MPa), and heated (100 °C) for 8 h. The reactor was cooled to ambient temperature and vented. A sample of the reaction mass was analyzed by HPLC. Results are given in Table G. G Summary of Reaction Parameters held constant: Pd:Ligand ratio 1:1; 3.0 eq. Et3N; 600 rpm; 100 °C; 8 h. CO Pd / C Pd / C Charge DPPF Charge Starting Material Compound 2a Exp. No. Pressure . . iii: Residual 2-bromo-4-chloro-6-methyl-benzeneamine in final reaction mass by HPLC. iv: Compound 2a in final reaction mass by HPLC. v: Ligand added as solution in p-dioxane. vi: 0.034 MPa. vii: 0.10 MPa. viii: 0.21 MPa. EXAMPLE 12 Preparation of 2-hydroxyethyl 2-amino-5-chloro-3-methylbenzoate (Compound 2a) using palladium on carbon and acetate to 1,1’-bis(diphenylphosphino)ferrocene at different ratios and temperatures. 2-Hydroxyethyl 2-amino-5-chloro-3-methylbenzoate was prepared in Experiments 62- 65 using the parameters in Table G below. Experiments 62-65 were conducted using a Biotage Endeavor pressure reactor system (8 x 8 mL). For each experiment a reaction vial was charged with the amount of 1,1’-bis(diphenylphosphino)ferrocene (DPPF) specified in Table G (11-5.5 mg, 0.010-0.020 mmol, 0.25-0.50 mol%) as a 110 mg / mL solution in dichloromethane (50-100 µL). A stream of nitrogen was passed over the solution to evaporate the solvent. The reaction vial was then charged with 10% palladium on carbon (Johnson Matthey, Type 10R39, 59.9% water-wet) (10.6 mg, 0.0040 mmol, 0.10 mol%), followed by the addition of a solution of 2-bromo-4-chloro-6-methylbenzeneamine (0.882 g, 4.00 mmol) and triethylamine (1.21 g, 12.0 mmol, 3.00 eq.) in ethylene glycol (4.48 g). The reactor was sealed and purged three times by pressurizing to 30-45 psig (0.21-0.31 MPa) with nitrogen followed by venting. The reaction mixture was agitated (600 rpm), pressurized with carbon monoxide (30 psig) (0.21 MPa), and heated (100 °C or 120 °C) for 8 h. The reactor was cooled to ambient temperature and vented. A sample of the reaction was analyzed by HPLC. Results are given in Table H. Table H Summary of Reaction Parameters held constant: 3.0 eq. Et3N; 30 psig (0.21 MPa) CO; 600 rpm; 16 h. DPPF Pd:Ligand Reaction Starting Pd / C Pd / C Charge Compound 2a Exp. No. Charge Ratio Temp. Material . iii: Residual 2-bromo-4-chloro-6-methyl-benzeneamine in final reaction mass by HPLC. iv: Compound 2a in final reaction mass by HPLC. EXAMPLE 13 Preparation of 2-hydroxyethyl 2-amino-5-chloro-3-methylbenzoate (Compound 2a) with palladium catalyst recycling. 2-Hydroxyethyl 2-amino-5-chloro-3-methylbenzoate was prepared in Experiments 66- 72 using the parameters in Table I below. Experiments 66-72 were conducted sequentially using a Biotage Endeavor pressure reactor system (8 x 8 mL). For Experiment 66 a reaction vial was charged with 1,1’- bis(diphenylphosphino)ferrocene (DPPF) (2.77 mg, 0.0050 mmol, 0.50 mol%), and 10% palladium on carbon (Johnson Matthey, Type 10R39, 59.9% water-wet) (13.3 mg, 0.0050 mmol, 0.50 mol%), followed by a solution of 2-bromo-4-chloro-6-methylbenzeneamine (0.220 g, 1.00 mmol) and triethylamine (0.304 g, 3.00 mmol, 3.00 eq.) in ethylene glycol (1.73 g). The reactor was sealed and purged three times by pressurizing to 30-45 psig (0.21-0.31 MPa) with nitrogen followed by venting. The reactor was agitated (600 rpm). The reactor was pressurized with carbon monoxide (30 psig) (0.21 MPa), heated to 100 °C and agitated under these conditions for 8 h. The reactor was allowed to cool to ambient temperature and vented. The reaction mass was centrifuged. The resultant supernatant liquid was decanted, leaving the catalyst residue in the reaction vial. The decanted liquid was analyzed by HPLC. Results are given in Table I. For Experiment 67, the catalyst residue of Experiment 66 was used as the palladium source. To the reaction vial containing the catalyst residue of Experiment 66 was added a solution of 2-bromo-4-chloro-6-methylbenzeneamine (0.220 g, 1.00 mmol) and triethylamine (0.304 g, 3.00 mmol, 3.00 eq.) in ethylene glycol (1.73 g). The reactor was sealed and purged three times by pressurizing to 30-45 psig 0.31 MPa) with nitrogen followed by venting. The reactor was agitated (600 rpm). The was pressurized with carbon monoxide (30 psig) (0.21 MPa), heated to 100 °C and agitated under these conditions for 8 h. The reactor was allowed to cool to ambient temperature and vented. The reaction mass was centrifuged. The resultant supernatant liquid was decanted, leaving the catalyst residue in the reaction vial. The decanted liquid was analyzed by HPLC. Results are given in Table I. For Experiments 68-52, the catalyst residue of the previous run was used as the palladium source. To the reaction vial containing the catalyst residue of each preceding experiment was added additional 1,1’-bis(diphenylphosphino)ferrocene (DPPF) (1.4 mg, 0.0025 mmol DPPF, 0.25 mol%) as a solution (27.7 mg / ml) in p-dioxane (50 µL), followed by a solution of 2-bromo-4-chloro-6-methylbenzeneamine (0.220 g, 1.00 mmol) and triethylamine (0.304 g, 3.00 mmol, 3.00 eq.) in ethylene glycol (1.73 g). The reactor was sealed and purged three times by pressurizing to 30-45 psig (0.21-0.31 MPa) with nitrogen followed by venting. The reactor was agitated (600 rpm). The reactor was pressurized with carbon monoxide (30 psig) (0.21 MPa), heated to 100 °C and agitated under these conditions for 8 or 16 h. The reactor was allowed to cool to ambient temperature and vented. The reaction mass was centrifuged. The resultant supernatant liquid was decanted, leaving the catalyst residue in the reaction vial. The decanted liquid was analyzed by HPLC. Results are given in Table I. Table I Summary of Reaction Parameters held constant: 3.0 eq. Et3N; 30 psig (0.21 MPa) CO; 600 rpm; 100 °C. Pd / C DPPF Reaction Starting Comp. v dium. ii: Versus 2-bromo-4-chloro-6-methylbenzeneamine starting material. iii: Residual 2-bromo-4-chloro-6-methyl-benzeneamine in final reaction mass by HPLC. iv: Compound 2a in final reaction mass by HPLC. v: No additional ligand was used in this experiment. vi: Reaction time was increased to 16 h in the final experiment. 14 Preparation of 2-amino-5-chloro-N,3- (Compound 1a). 2-Amino-5-chloro-N,3-dimethylbenzamide was prepared in Experiments 73-88 using the parameters in Table J below. Experiments 73-88 were conducted using a Biotage Endeavor pressure reactor system (8 x 8 mL). For each experiment a reaction vial was charged with a reaction mass sample containing 2-hydroxyethyl 2-amino-5-chloro-3-methylbenzoate (Compound 2a) (1.00 mL containing 0.153 g, 0.667 mmol of Compound 2a) and the amount of methylamine (40% solution in ethylene glycol) specified in Table J (0.104-0.207 g, 1.34- 2.67 mmol, 2.0-4.0 eq.). The reactor was sealed and purged five times by pressurizing to 30-45 psig (0.21-0.31 MPa) with nitrogen followed by venting. The reaction mixture was agitated (600 rpm), and purged five additional times by pressurizing to 45 psig (0.31 MPa) with nitrogen followed by venting. The reactor was heated (80 °C or 120 °C), and agitated for 2-16 h. The reactor was cooled to ambient temperature and vented. A sample of the reaction mass was analyzed by HPLC. Results are given in Table J. Table J Methylamine Reaction Reaction Starting Material Compound 1a Exp. No. i °ii iii ii. Residual Compound 2a in final reaction mass by HPLC. iii. Compound 1a product in final reaction mass by HPLC. 15 Preparation of 2-amino-5-chloro-N,3- (Compound 1a). 2-Amino-5-chloro-N,3-dimethylbenzamide was prepared in Experiments 89-93 using the parameters in Table K below. Experiments 89-93 were conducted using a 25 mL Parr pressure reactor. For each experiment the reactor was charged with a reaction mass sample containing 2-hydroxyethyl 2-amino-5-chloro-3-methylbenzoate (Compound 2a) (10.0 mL containing 1.53 g, 6.67 mmol of Compound 2a) and the amount of methylamine (40% solution in ethylene glycol) specified in Table J (2.59-5.18 g, 33.4-66.7 mmol, 5.0-10.0 eq.). The reactor was sealed and purged five times by pressurizing to 30-45 psig 0.21-0.31 MPa) with nitrogen followed by venting. The reaction mixture was agitated (300 rpm), and purged five additional times by pressurizing to 30-45 psig 0.21-0.31 MPa) with nitrogen followed by venting. The reactor was heated (80 °C or 120 °C), and agitated for 3- 72 h. The reactor was cooled to ambient temperature and vented. A sample of the reaction mass was analyzed by HPLC. Results are given in Table K. Table K Methylamine Reaction Reaction Starting Material Compound 1a Exp. No. i °ii iii ii: Residual Compound 2a in final reaction mass by HPLC. iii: Compound 1a product in final reaction mass by HPLC. By the procedures described herein together with methods known in the art, the compounds disclosed in the Tables that follow can be prepared. In Table 1 and the following tables: t means tertiary, s means secondary, n means normal, i means iso, c means cyclo, Me means methyl, Et means ethyl, Pr means propyl, Bu means butyl, MeO- means methoxy, EtO- means ethoxy, and i-PrO means isopropoxy. Concatenations of groups are abbreviated similarly; for example, “c-PrCH2” means cyclopropylmethyl. A dash (i.e. “-”) in a structure fragment denotes the attachment point of the fragment to the remainder of the molecule.R1is Me, R2is H, R3is Cl, R4is H.Z Z Z HOCH CH O- H N- (n-Bu)HN- (c-hex l)HN-- - T e presen scosure aso ncues a es roug , eac o which is constructed the same as Table 1 above, except that the row heading in Table 1 (i.e. “R1is Me, R2is H, R3is Cl, R4is H”) is replaced with the respective row headings shown below. Table Row Heading Table Row Heading HFFllClHHisFFFCl Table Row Heading 34A R1is OCF3, R2is H, R3is F, R4is Clenzoate compounds of Formula 2 of the present disclosure can be used to prepare a wide variety of 2-aminobenzamide compounds of Formula 1 that are useful as intermediates for the preparation of crop protection agents. In another aspect of the present invention compounds of the Formula 1 prepared by the method of Scheme 1 are useful as intermediates for preparing compounds of Formula 6. Compounds of Formula 6 are useful as insecticides, as previously disclosed in WO 2003 / 015518 and WO 2006 / 055922. Compounds of Formula 6 can be prepared from compounds of Formula 1 by a variety of processes previously disclosed in WO 2003 / 016283, WO 2004 / 067528, WO 2004 / 087689 and WO 2006 / 062978.

Claims

What is claimed is:

1. A method for preparing a compound of Formula 1 whereinR1is F, Cl, cyano, C1–C4alkyl, C1–C4haloalkyl, C1–C4alkoxy or C1–C6haloalkoxy; R2is H, F, Cl or cyano; R3is F, Cl or cyano; R4is H, F, Cl or cyano; R5is H, C1–C4alkyl, C3–C6cycloalkyl, C4–C7cycloalkylalkyl, C4–C7alkylcycloalkyl or cyclopropylcyclopropyl; and the method comprising: (I) forming a mixture comprising: (A) a compound of Formula 2, wherein R1is F, Cl, C1–C4alkyl, C1–C4haloalkyl, C1–C4alkoxy or C1–C6haloalkoxy; R2is H, F, Cl or cyano; R3is F, Cl or cyano; R4is H, F, Cl or cyano; R6is C1–C14alkyl, C2–C14hydroxyalkyl, C3–C14dialkylaminoalkyl, or C3–C14halodialkylaminoalkyl); and wherein the compound of Formula 2 is prepared to a method comprising:(1) forming a (a) a Formula 3, wherein R1is F, Cl, C1–C4alkyl, C1–C4haloalkyl, C1–C4alkoxy or C1–C6haloalkoxy; R2is H, F, Cl or cyano; R3is F, Cl or cyano; R4is H, F, Cl or cyano; X is Br or I; and (b) a palladium source; (c) a ligand; (d) a base; (e) carbon monoxide; and (f) a compound of Formula 4 , wherein R6is C1–C14alkyl, C2–C14hydroxyalkyl, C3–C14dialkylaminoalkyl, or C3–C14halodialkylaminoalkyl); and (2) reacting the mixture; and (B) a compound of Formula 5 , wherein R5is H, C1–C4alkyl, C3–C6cycloalkyl, C4–C7cycloalkylalkyl, C4–C7alkylcycloalkyl or cyclopropylcyclopropyl; and (II) reacting the mixture.

2. The method of Claim 1 is Cl or methyl; R2is H; R3is Cl or cyano; and R4is H, F, Cl.

3. The method of Claim 2 wherein R1is methyl; R3is Cl or cyano; and R4is H.

4. The method of Claim 3 wherein R3is cyano.

5. The method of Claim 1 wherein the compound of Formula 1 is the compound of Formula 1a the method comprising:(I) forming a mixture comprising: (A) a compound of Formula 2 wherein the compound of Formula 2 is the compound of Formula 2a , wherein theto a method comprising: (1) forming a mixture comprising: (a) a compound of Formula 3 wherein the compound of Formula 3 is a compound of Formula 3a ,wherein or(b) a palladium (c) a ligand; (d) a base; (e) carbon monoxide; and (f) a compound of Formula 4 , wherein R6is 2-hydroxyethyl; and (2) reacting the mixture; and (B) a compound of Formula 5 , wherein R5is methyl; and (II) reacting the mixture.

6. A method for preparing a compound of Formula 2, wherein R1is F, Cl, C1–C4alkyl, C1–C4haloalkyl, C1–C4alkoxy or C1–C6haloalkoxy; R2is H, F, Cl or cyano; R3is F, Cl or cyano; R4is H, F, Cl or cyano; R6is C1–C14alkyl, C2–C14hydroxyalkyl, C3–C14dialkylaminoalkyl, or C3–C14halodialkylaminoalkyl); and wherein the compound of Formula 2 is prepared to a method comprising: (1) forming a mixture comprising: (a) a compound of Formula 3, wherein R1is F, Cl, C1–C4alkyl, C1–C4haloalkyl, C1–C4alkoxy or C1–C6haloalkoxy; R2is H, F, Cl or cyano; R3is F, Cl or cyano; R4is H, F, Cl or cyano; X is Br or I; and (b) a palladium source; (c) a ligand; (d) a base; (e) carbon monoxide; and (f) a compound of Formula 4 , wherein R6is C1–C14alkyl, C2–C14hydroxyalkyl, C3–C14dialkylaminoalkyl, or C3–C14halodialkylaminoalkyl); and (2) reacting the mixture.

7. The method of Claim 6 wherein R1is Cl or methyl; R2is H; R3is Cl or cyano; and R4is H, F, Cl.

8. The method of Claim 7 wherein R1is methyl; R3is Cl or cyano; and R4is H.

9. The method of Claim 8 wherein R3is cyano.

10. The method of Claim 6 wherein the compound of Formula 2 is a compound of Formula 2a, wherein the to a method comprising: (1) forming a mixture comprising: (a) a compound of Formula 3 wherein the compound of Formula 3 is a compound of Formula 3a, wherein X is Br or I; and (b) a palladium source; (c) a ligand; (d) a base; (e) carbon monoxide; and (f) a compound of Formula 4 , wherein R6is 2-hydroxyethyl; and (2) reacting the mixture.

11. The method of any one of Claims 1 to 10 wherein X is Br.

12. The method of any one of Claims 1 to 10 wherein the effective catalyst loading of the palladium source relative to the compound of Formula 3 is less than 0.1 mol%.

13. The method of any one of Claims 1 to 10 wherein the mole ratio of the palladium to ligand is at least about 1:0.5.

14. The method of any one of 1 to 10 wherein the palladium source is a soluble palladium compound selected from palladium(II) acetate, palladium(II) trifluoroacetate, palladium(II) propionate, palladium(II) benzoate, palladium(II) chloride, palladium(II) bromide, palladium(II) sulfate, (dibenzylideneacetone)dipalladium(0) and palladium(II) acetylacetonate; and the ligand is a bidentate bisphosphine ligand selected from 1,1'-bis(diphenylphosphino)ferrocene, 1,4-bis(diphenylphosphino)butane, 1,1’-bis(diphenylphosphino)propane, and 9,9-dimethyl-4,5-bis(diphenyl- phosphino)xanthene.

15. The method of Claim 14 wherein the palladium source is a soluble palladium compound selected from palladium(II) acetate and palladium(II) chloride.

16. The method of any one of Claims 1 to 10 wherein the palladium source on an insoluble support is selected from palladium on carbon and palladium (II) hydroxide on carbon; and the ligand is a bidentate bisphosphine ligand selected from 1,1'-bis(diphenylphosphino)ferrocene, 1,4-bis(diphenylphosphino)butane, 1,1’-bis(diphenylphosphino)propane, and 9,9-dimethyl-4,5-bis(diphenyl- phosphino)xanthene.

17. The method of Claim 16 wherein the palladium source on an insoluble support is palladium on carbon.

18. The method of Claim 16 further comprising the steps: (3) separating the reacted palladium source from the mixture, after Step (2) reacting the mixture; (4) recycling the separated palladium source of Step (3) to Step (1) as (b) the palladium source; and (5) repeating Steps (1) through (3) using the recycled palladium source at least one time.

19. The method of any one of Claims 1 to 10 wherein the reacting is performed in a suitable solvent comprising ethylene glycol and N,N-dimethylethanolamine.

20. A method for preparing a compound of Formula 6 , wherein Y1is aY2is hydrogen, halogen, cyano, C1-C4alkyl or C1-C4haloalkyl; each Y3is independently halogen, cyano, C1-C4alkyl or C1-C4haloalkyl; n is 0, 1, 2 or 3; R1is F, Cl, C1–C4alkyl, C1–C4haloalkyl, C1–C4alkoxy or C1–C6haloalkoxy; R2is H, F, Cl or cyano; R3is F, Cl or cyano; R4is H, F, Cl or cyano; R5is H, C1–C4alkyl, C3–C6cycloalkyl, C4–C7cycloalkylalkyl, C4–C7alkylcycloalkyl or cyclopropylcyclopropyl; using a compound of Formula 1, the method characterized by preparing the compound of Formula 1 using the method of Claim 1 or Claim 10.

21. The method of Claim 20 wherein the compound of Formula 6 is chlorantraniliprole or cyantraniliprole.

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