A NEW EFFICIENT PROCESS FOR THE SYNTHESIS OF 2-AMINO-5-CHLOR-N,3-DIMETHYLBENZAMIDE

MX435077BActive Publication Date: 2026-06-12FMC IP TECH GMBH +1

Patent Information

Authority / Receiving Office
MX · MX
Patent Type
Patents
Current Assignee / Owner
FMC IP TECH GMBH
Filing Date
2022-04-29
Publication Date
2026-06-12

AI Technical Summary

Technical Problem

Conventional processes for synthesizing 2-amino-5-chloro-N,3-dimethylbenzamide are costly, hazardous, and involve complex operations with lengthy steps and significant waste generation.

Method used

A novel method involving the sequential or combined use of halogenation, oxidation, and alkylation reactions in controlled solvent and catalyst environments to produce 2-amino-5-chloro-N,3-dimethylbenzamide, reducing the number of steps and eliminating the need for mixed solvent separations.

Benefits of technology

The method significantly reduces costs, minimizes waste, and simplifies operations while maintaining high purity and yield of the target compound.

✦ Generated by Eureka AI based on patent content.
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Abstract

This paper describes novel methods for synthesizing 2-amino-5-chloro-N,3-dimethylbenzamide. The compounds prepared by the methods disclosed herein are useful for the preparation of certain anthranilamide compounds of interest as insecticides, such as, for example, the insecticides chlorantraniliprole and cyantraniliprole.
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Description

A NEW EFFICIENT PROCESS FOR THE SYNTHESIS OF 2-AMINO-5-CHLOR-N,3-DIMETHYLBENZAMIDE Rzzcnn / zznz / E / YiAi CROSS REFERENCE TO A RELATED APPLICATION This application claims the benefit of U.S. Provisional Application No. 62 / 929 138 filed on November 1, 2019. FIELD OF INVENTION This disclosure relates to novel methods for synthesizing 2-amino-5-chloro-N,3-dimethylbenzamide. The compounds prepared by the methods disclosed herein are useful for the preparation of certain anthranilamide compounds of interest as insecticides, such as, for example, the insecticides chlorantraniliprole and cyantraniliprole. BACKGROUND Conventional processes for the production of 2-amino-5-chloro-N,3-dimethylbenzamide present several problems at an industrial level, such as hazardous materials, high cost, relatively long method steps, and complicated operations. This disclosure provides novel methods for preparing 2-amino-5-chloro-N,3-dimethylbenzamide and derivatives thereof. The benefits of the methods described herein compared to previous methods are numerous and include reduced cost, elimination of the need for mixed solvent separations, reduced waste, relatively short method steps, simplified operational complexity, and reduced process risks. BRIEF DESCRIPTION In one respect, a method is provided herein for preparing a compound of Formula VI, where Rn (Formula VI) each of R? - Rio is independently selected from hydrogen, halogen, halogenated C1-C5 alkyl and C1-C5 alkyl; wherein at least one of R7-R10 is a halogen; and wherein Rn is selected from branched C1-C10 alkyl and unbranched C1-C10 alkyl, the method comprising I) form a mixture comprising A) a compound of Formula V, where Rzzcnn / zznz / E / viAi (Formula V) each of FU - R10 is independently selected from hydrogen, halogen, halogenated C1-C5 alkyl and C1-C5 alkyl; wherein at least one of R7-R10 is a halogen; and wherein the compound of Formula V is prepared according to a method comprising i) form a first mixture comprising a) a compound of Formula III, where each of Ri - FU is independently selected from hydrogen, halogen and C1-C5 alkyl; b) a solvent; and c) a halogenation reagent; i) react the first mixture; (ii) introducing a second mixture into the first mixture to form a third mixture, the second mixture comprising (iv) B) C) d) an oxidizing agent; and e) a catalyst; and react the third mixture; an alkylamine; and a solvent; and react the mixture. In one aspect, a method is provided herein for preparing a compound of Formula V, wherein Rzzcnn / zznz / E / YiAi (Formula V) each of R? - Rio is independently selected from hydrogen, halogen, halogenated C1-C5 alkyl and C1-C5 alkyl; and wherein at least one of R7-R10 is a halogen, comprising the method I) form a first mixture comprising A) a compound of Formula III, where each of R1 - R4 is independently selected from hydrogen, halogen and C1-C5 alkyl; B) a solvent; and C) a halogenation reagent; II) react the first mixture; III) introducing a second mixture into the first mixture to form a third mixture, the second mixture comprising D) an oxidizing agent; and E) a catalyst; and IV) react the third mixture. In one respect, a method is provided herein for preparing a compound of Formula VI, where Rn Rzzcnn / zznz / E / YiAi (Formula VI) each of R7 - Rio is independently selected from hydrogen, halogen, halogenated C1-C5 alkyl and C1-C5 alkyl; wherein at least one of R7-R10 is a halogen; and wherein Rn is selected from branched C1-C10 alkyl and unbranched C1-C10 alkyl, the method comprising I) form a mixture comprising A) a compound of Formula V, where (Formula V) each of R7 - R10 is independently selected from hydrogen, halogen, halogenated C1-C5 alkyl and C1-C5 alkyl; wherein at least one of R7-R10 is a halogen; and wherein the compound of Formula V is prepared according to a method comprising i) form a mixture comprising a) a compound of Formula IV, where (Formula IV) each of R? - Rio is independently selected from hydrogen, halogen, C1-C5 halogenated alkyl and C1-C5 alkyl; and wherein at least one of R7-R10 is a halogen; b) an oxidizing agent; c) a solvent; and d) a catalyst; and i) react the mixture; B) an alkylamine; and C) a solvent; and II) to react the mixture. In one aspect, a method is provided herein for preparing a compound of Formula V, wherein Rzzcnn / zznz / E / viAi (Formula V) each of R7 - R10 is independently selected from hydrogen, halogen, halogenated C1-C5 alkyl and C1-C5 alkyl; and wherein at least one of R7-R10 is a halogen, the method comprising I) form a mixture comprising A) a compound of Formula IV, where (Formula IV) each of R7 - R10 is independently selected from hydrogen, halogen, halogenated C1-C5 alkyl and C1-C5 alkyl; and wherein at least one of R7-R10 is a halogen; B) an oxidizing agent; C) a solvent; and D) a catalyst; and II) to react the mixture. In one aspect, a method is provided herein for preparing a compound of Formula IV, wherein Rzzcnn / zznz / E / YiAi (Formula IV) each of R7 - R10 is independently selected from hydrogen, halogen, halogenated C1-C5 alkyl and C1-C5 alkyl; wherein at least one of R7-R10 is a halogen, comprising the method I) form a mixture comprising A) a compound of Formula III, where each of Ri - FU is independently selected from hydrogen, halogen and C1-C5 alkyl; B) C) a solvent; a halogenation reagent; and react the mixture. In one respect, a method is provided herein for preparing a compound of Formula III, where Rzzcnn / zznz / E / YiAi each of Ri - FU is independently selected from hydrogen, halogen and C1-C5 alkyl, comprising the method I) form a mixture comprising A) a compound of Formula II, where OH (Formula II) each of R1 - R5 is independently selected from hydrogen, halogen and C1-C5 alkyl; and wherein the compound of Formula II is prepared according to a method comprising i) forming a mixture comprising a) a compound of Formula I, where (Formula I) each of R1 - R5 is independently selected from hydrogen, halogen and C1-C5 alkyl; b) Doral hydrate; c) a hydroxylamine derivative; d) a solvent; e) an inorganic salt; and f) an acid; and i) react the mixture; and B) an acid; and II) to react the mixture. In one respect, a method is provided herein for preparing a compound of Formula II, where Rzzcnn / zznz / E / viAi (Formula II) each of Ri - Rs is independently selected from hydrogen, halogen and C1-C5 alkyl, comprising the method I) form a mixture comprising A) a compound of Formula I, where (Formula I) each of R1 - R5 is independently selected from hydrogen, halogen and C1-C5 alkyl; B) Doral hydrate; C) a hydroxylamine derivative; D) a solvent; E) an inorganic salt; and F) an acid; and II) to react the mixture. In one respect, a method is provided herein for preparing a compound of Formula IV, where Azzcnn / zznz / E / YiAi each of R? - Rio is independently selected from hydrogen, halogen, halogenated C1-C5 alkyl and C1-C5 alkyl; wherein at least one of R7-R10 is a halogen, comprising the method I) form a mixture comprising A) a compound of Formula II, where each of R1 - R5 is independently selected from hydrogen, halogen and C1-C5 alkyl; and B) an acid; II) react the first mixture; III) introducing a halogenating reagent into the first mixture to form a second mixture; and IV) react the second mixture. DETAILED DESCRIPTION OF THE DISCLOSURE As used herein, the terms “comprises,” “comprising,” “includes,” “having,” “containing,” “characterized by,” or any variation thereof, are intended to encompass a non-exclusive inclusion, subject to any limitations explicitly stated. For example, a composition, mixture, process, or method comprising a list of elements is not necessarily limited to those elements alone, but may include other elements not expressly listed or inherent in such composition, mixture, process, or method. The transitional phrase “consisting of” excludes any unspecified element, step, or ingredient. If it were in the claim, it would preclude the inclusion of materials other than those mentioned, except for impurities commonly associated with them. When the phrase “consisting of” appears in a clause within the body of a claim, rather than immediately following the preamble, it limits only the element set forth in that clause; other elements of the claim as a whole are not excluded. The transitional expression “essentially consisting of” is used to define a composition or method that includes materials, steps, features, components, or elements, in addition to those explicitly disclosed, provided that these additional materials, steps, features, components, or elements do not materially affect the basic and novel feature(s) of the claimed invention. The term “essentially consisting of” occupies an intermediate position between “comprising” and “consisting of.” When an invention or part thereof is defined by an open term such as “comprising”, it is readily understood that (unless otherwise stated) the description should also be interpreted as describing such an invention using the terms “consisting essentially of” or “consisting of”. Furthermore, unless explicitly stated otherwise, “or” refers to an inclusive or, not 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). Furthermore, it is intended that the indefinite articles “a” and “one” preceding an element or component of the invention should not be restrictive with respect to the number of instances (i.e., occurrences) of the element or component. Therefore, “a” or “one” should be interpreted to include one or at least one, and the singular form of the word for the element or component should also include the plural, unless it is clear that the number is singular. As used herein, the term “approximately” means more or less than 10% of the value. The term “halogen,” whether used alone or in compound words such as “haloalkyl,” includes fluorine, chlorine, bromine, or iodine. Furthermore, when used in compound words such as “haloalkyl,” the alkyl group may be partially or fully substituted with halogen atoms, which may be the same or different. When a group contains a substituent that can be hydrogen, for example, R4, then when this substituent is considered to be hydrogen, it is recognized that this is equivalent to the group not being substituted. The term “alkyl” includes, without limitation, any functional group comprising linear or branched alkyl chains. In some respects, the alkyl may be methyl, ethyl, n-propyl, isopropyl, or the various isomers of butyl, pentyl, or hexyl. Certain compounds of this invention may exist as one or more stereoisomers. The various stereoisomers include enantiomers, diastereomers, atropisomers, and geometric isomers. A person skilled in the art will appreciate that one stereoisomer may be more active and / or may exhibit beneficial effects when enriched with respect to another stereoisomer. Rzzcnn / zznz / E / YiAi stereoisomers, or when it is separated from the other stereoisomer or stereoisomers. Additionally, the expert knows how to selectively separate, enrich, and / or prepare said stereoisomers. The achievements of this disclosure include: Implementation 1. A method for preparing a compound of Formula VI, wherein Rzzcnn / zznz / E / YiAi R11 (Formula VI) each of R7 - R10 is independently selected from hydrogen, halogen, halogenated C1-C5 alkyl and C1-C5 alkyl; wherein at least one of R7-R10 is a halogen; and wherein Rn is selected from branched C1-C10 alkyl and unbranched C1-C10 alkyl, the method comprising I) form a mixture comprising A) a compound of Formula V, where (Formula V) each of R7 - Rio is independently selected from hydrogen, halogen, halogenated C1-C5 alkyl and C1-C5 alkyl; wherein at least one of R7-R10 is a halogen; and wherein the compound of Formula V is prepared according to a method comprising i) form a first mixture comprising a) a compound of Formula III, where Rzzcnn / zznz / E / viAi each of Ri - FU is independently selected from hydrogen, halogen and C1-C5 alkyl; b) a solvent; and c) a halogenation reagent; ii) react the first mixture; iii) introducing a second mixture into the first mixture to form a third mixture, the second mixture comprising d) an oxidizing agent; and e) a catalyst; and iv) react the third mixture; B) an alkylamine; and C) a solvent; and II) to react the mixture. Embodiment 2. The method of embodiment 1, wherein the alkylamine comprises a functional group selected from branched C1-C10 alkyl and unbranched C1-C10 alkyl. Realization 3. The method of realization 2, wherein the alkylamine is selected from methylamine, ethylamine, propylamine, isopropylamine, butylamine, t-butylamine and combinations thereof. Realization 4. The method of realization 3, wherein the alkylamine is methylamine. Implementation 5. The method of implementation 1, wherein solvent C) is selected from acetonitrile, dichloroethane, toluene, chlorobenzene, xylene, methanol, ethanol, isopropanol, ethyl acetate, isopropyl acetate, and combinations thereof. Implementation 6. The method of implementation 5, wherein the solvent C) is ethyl acetate. Implementation 7. The method of implementation 1, wherein step II) of the method, which consists of reacting the mixture, occurs at a reaction temperature in the range of approximately 0 °C to approximately 100 °C. Implementation 8. The method of implementation 7, wherein step II) of the method, which consists of reacting the mixture, occurs at a reaction temperature in the range of approximately 20 °C to approximately 30 °C. Implementation 9. The method of implementation 1, wherein the solvent b) is selected from acetonitrile, dichloroethane, toluene, chlorobenzene, xylene, acetic acid, acetic anhydride, propionic acid, butyric acid, and combinations thereof. Realization 10. The method of realization 9, wherein the solvent b) is acetic acid. Realization 11. The method of realization 1, wherein the halogenation reagent is selected from a chlorination reagent, a bromination reagent, an iodination reagent, and combinations thereof. Implementation 12. The method of implementation 11, wherein the chlorinating reagent is selected from chlorine, thionyl chloride, phosgene, diphosgene, triphosgene, oxalyl chloride, sulfuryl chloride, phosphorus trichloride, phosphorus oxychloride, trichloroisocyanuric acid, and combinations thereof. Realization 13. The method of realization 12, wherein the chlorinating reagent is sulfuryl chloride. Implementation 14. The method of implementation 1, wherein step ii) of the method, which consists of reacting the first mixture, occurs at a reaction temperature in the range of approximately 20 °C to approximately 140 °C. Implementation 15. The method of implementation 14, wherein step i) of the method, which consists of reacting the first mixture, occurs at a reaction temperature in the range of approximately 120 °C to approximately 130 °C. Implementation 16. The method of implementation 1, wherein the oxidizing agent is selected from oxygen, chlorine, sodium hypochlorite, chromium trioxide, 3-chloroperoxybenzoic acid, hydrogen peroxide, peroxyacetic acid, potassium peroxymonosulfate, potassium permanganate, and combinations thereof. Realization 17. The method of realization 16, wherein the oxidizing agent is hydrogen peroxide. Realization 18. The method of realization 1, wherein the catalyst is selected from sulfuric acid, hydrogen chloride, nitric acid, and combinations thereof. Realization 19. The method of realization 18, wherein the catalyst is sulfuric acid. Implementation 20. The method of implementation 1, wherein step iv) of the method, which consists of reacting the third mixture, occurs at a reaction temperature in the range of approximately 20 °C to approximately 100 °C. Implementation 21. The method of implementation 20, wherein step iv) of the method, which consists of reacting the third mixture, occurs at a reaction temperature in the range of approximately 60 °C to approximately 65 °C. Embodiment 22. The method of embodiment 1, wherein the compound of Formula III is prepared according to a method comprising I) form a mixture comprising A) a compound of Formula II, where Rzzcnn / zznz / E / YiAi Rzzcnn / zznz / E / YiAi each of Ri - Rs is independently selected from hydrogen, halogen and C1-C5 alkyl; and wherein the compound of Formula II is prepared according to a method comprising i) forming a mixture comprising a) a compound of Formula I, where each of R1 - R5 is independently selected from hydrogen, halogen and C1-C5 alkyl; b) Doral hydrate; c) a hydroxylamine derivative; d) a solvent; e) an inorganic salt; and f) an acid; and i) react the mixture; and B) an acid; and II) to react the mixture. Realization 23. The method of realization 22, wherein acid B) is selected from hydrochloric acid, sulfuric acid, nitric acid, acetic acid, and combinations thereof. Realization 24. The method of realization 23, wherein acid B) is hydrochloric acid. Implementation 25. The method of implementation 22, wherein step II) of the method, which consists of reacting the mixture, occurs at a reaction temperature in the range of approximately 10 °C to approximately 90 °C. Implementation 26. The method of implementation 25, wherein step II) of the method, which consists of reacting the mixture, occurs at a reaction temperature in the range of approximately 60 °C to approximately 65 °C. Realization 27. The method of realization 22, wherein the hydroxylamine derivative is selected from hydroxylamine sulfate, hydroxylamine hydrochloride, and combinations thereof. Realization 28. The method of realization 27, wherein the hydroxylamine derivative is hydroxylamine sulfate. Realization 29. The method of realization 22, wherein the solvent is selected from methanol, ethanol, toluene, water, and combinations thereof. Realization 30. The method of realization 29, wherein the solvent is water. Realization 31. The method of realization 22, wherein the inorganic salt is selected from sodium sulfate, sodium hydrogen sulfate, sodium chloride, sodium disulfite, potassium sulfate, potassium chloride, and combinations thereof. Realization 32. The method of realization 31, wherein the inorganic salt is sodium sulfate. Realization 33. The method of realization 22, wherein the acid f) is selected from hydrochloric acid, sulfuric acid, nitric acid, hydrobromic acid, formic acid, acetic acid, and combinations thereof. Realization 34. The method of realization 33, wherein the acid f) is hydrochloric acid. Realization 35. The method of realization 22, wherein the concentration of the compound of Formula I in the mixture varies from approximately 1% to approximately 30%. Realization 36. The method of realization 35, wherein the concentration of the compound of Formula I in the mixture is in the range of approximately 3% to approximately 10%. Implementation 37. The method of implementation 22, wherein step i) of the method, which consists of reacting the mixture, occurs at a reaction temperature in the range of approximately 10 °C to approximately 100 °C. Implementation 38. The method of implementation 37, wherein step i) of the method, which consists of reacting the mixture, occurs at a reaction temperature in the range of approximately 50 °C to approximately 55 °C. Implementation 39. A method for preparing a compound of Formula V, wherein Rzzcnn / zznz / E / YiAi r7(Formula V) each of R? - Rw is independently selected from hydrogen, halogen, halogenated C1-C5 alkyl and C1-C5 alkyl; and wherein at least one of R7-R10 is a halogen, the method comprising I) form a first mixture comprising A) a compound of Formula III, where Rzzcnn / zznz / E / viAi each of Ri - R4 is independently selected from hydrogen, halogen and C1-C5 alkyl; B) a solvent; and C) a halogenation reagent; II) react the first mixture; III) introducing a second mixture into the first mixture to form a third mixture, the second mixture comprising D) an oxidizing agent; and E) a catalyst; and IV) react the third mixture. Implementation 40. The method of implementation 39, wherein the solvent is selected from acetonitrile, dichloroethane, toluene, chlorobenzene, xylene, acetic acid, acetic anhydride, propionic acid, butyric acid, and combinations thereof. Realization 41. The method of realization 40, wherein the solvent is acetic acid. Realization 42. The method of realization 39, wherein the halogenating reagent is selected from a chlorinating reagent, a brominating reagent, an iodinating reagent, and combinations thereof. Implementation 43. The method of implementation 42, wherein the chlorinating reagent is selected from chlorine, thionyl chloride, phosgene, diphosgene, triphosgene, oxalyl chloride, sulfuryl chloride, phosphorus trichloride, phosphorus oxychloride, trichloroisocyanuric acid, and combinations thereof. Realization 44. The method of realization 43, wherein the chlorinating reagent is sulfuryl chloride. Implementation 45. The method of implementation 39, wherein step II) of the method, which consists of reacting the first mixture, occurs at a reaction temperature in the range of approximately 20 °C to approximately 140 °C. Implementation 46. The method of implementation 45, wherein step II) of the method, which consists of reacting the first mixture, occurs at a reaction temperature in the range of approximately 120 °C to approximately 130 °C. Implementation 47. The method of implementation 39, wherein the oxidizing agent is selected from oxygen, chlorine, sodium hypochlorite, chromium trioxide, 3-chloroperoxybenzoic acid, hydrogen peroxide, peroxyacetic acid, potassium peroxymonosulfate, potassium permanganate, and combinations thereof. Realization 48. The method of realization 47, wherein the oxidizing agent is hydrogen peroxide. Realization 49. The method of realization 39, wherein the catalyst is selected from sulfuric acid, hydrogen chloride, nitric acid, and combinations thereof. Realization 50. The method of realization 49, wherein the catalyst is sulfuric acid. Implementation 51. The method of implementation 39, wherein step IV) of the method, which consists of reacting the third mixture, occurs at a reaction temperature in the range of approximately 20 °C to approximately 100 °C. Implementation 52. The method of implementation 51, wherein step IV) of the method, which consists of reacting the third mixture, occurs at a reaction temperature in the range of approximately 60 °C to approximately 65 °C. Embodiment 53. The method of embodiment 39, wherein the compound of Formula III is prepared according to a method comprising I) form a mixture comprising A) a compound of Formula II, where Rzzcnn / zznz / E / YiAi OH (Formula II) each of Ri - Rs is independently selected from hydrogen, halogen and C1-C5 alkyl; and wherein the compound of Formula II is prepared according to a method comprising i) forming a mixture comprising a) a compound of Formula I, where (Formula I) each of R1 - Rs is independently selected from hydrogen, halogen and C1-C5 alkyl; b) Doral hydrate; c) a hydroxylamine derivative; d) a solvent; e) an inorganic salt; and f) an acid; and ii) react the mixture; and B) an acid; and II) to react the mixture. Realization 54. The method of realization 53, wherein acid B) is selected from hydrochloric acid, sulfuric acid, nitric acid, acetic acid, and combinations thereof. Realization 55. The method of realization 54, wherein acid B) is hydrochloric acid. Implementation 56. The method of implementation 53, wherein step II) of the method, which consists of reacting the mixture, occurs at a reaction temperature in the range of approximately 10 °C to approximately 90 °C. Implementation 57. The method of implementation 56, wherein step II) of the method, which consists of reacting the mixture, occurs at a reaction temperature in the range of approximately 60 °C to approximately 65 °C. Implementation 58. The method of implementation 53, wherein the hydroxylamine derivative is selected from hydroxylamine sulfate, hydroxylamine hydrochloride, and combinations thereof. Realization 59. The method of realization 58, wherein the hydroxylamine derivative is hydroxylamine sulfate. Implementation 60. The method of implementation 53, wherein the solvent is selected from methanol, ethanol, toluene, water, and combinations thereof. Realization 61. The method of realization 60, wherein the solvent is water. Realization 62. The method of realization 53, wherein the inorganic salt is selected from sodium sulfate, sodium hydrogen sulfate, sodium chloride, sodium disulfite, potassium sulfate, potassium chloride, and combinations thereof. Realization 63. The method of realization 62, wherein the inorganic salt is sodium sulfate. Realization 64. The method of realization 53, wherein the acid f) is selected from hydrochloric acid, sulfuric acid, nitric acid, hydrobromic acid, formic acid, acetic acid, and combinations thereof. Realization 65. The method of realization 64, wherein the acid f) is hydrochloric acid. Realization 66. The method of realization 53, wherein the concentration of the compound of Formula I in the mixture varies from approximately 1% to approximately 30%. Realization 67. The method of realization 66, wherein the concentration of the compound of Formula I in the mixture is in the range of approximately 3% to approximately 10%. Implementation 68. The method of implementation 53, wherein step ii) of the method, which consists of reacting the mixture, occurs at a reaction temperature in the range of approximately 10 °C to approximately 100 °C. Rzzcnn / zznz / E / viAi Embodiment 69. The method of embodiment 68, wherein step ii) of the method, which consists of reacting the mixture, occurs at a reaction temperature in the range of approximately 50 °C to approximately 55 °C. Implementation 70. A method for preparing a compound of Formula VI, wherein Rzzcnn / zznz / E / YiAi R11 (Formula VI) each of R7 - R10 is independently selected from hydrogen, halogen, halogenated C1-C5 alkyl and C1-C5 alkyl; wherein at least one of R7-R10 is a halogen; and wherein Rn is selected from branched C1-C10 alkyl and unbranched C1-C10 alkyl, the method comprising I) form a mixture comprising A) a compound of Formula V, where (Formula V) each of R? - Rio is independently selected from hydrogen, halogen, halogenated C1-C5 alkyl and C1-C5 alkyl; wherein at least one of R7-R10 is a halogen; and wherein the compound of Formula V is prepared according to a method comprising i) form a mixture comprising a) a compound of Formula IV, where Rzzcnn / zznz / E / YiAi (Formula IV) each of R? - Rio is independently selected from hydrogen, halogen, C1-C5 halogenated alkyl and C1-C5 alkyl; and wherein at least one of R7-R10 is a halogen; b) c) d) an oxidizing agent; a solvent; and a catalyst; and i) react the mixture; B) an alkylamine; and C) a solvent; and II) to react the mixture. Embodiment 71. The method of embodiment 70, wherein the alkylamine comprises a functional group selected from branched C1-C10 alkyl and unbranched C1-C10 alkyl. Implementation 72. The method of implementation 71, wherein the alkylamine is selected from methylamine, ethylamine, propylamine, isopropylamine, butylamine, i-butylamine and combinations thereof. Realization 73. The method of realization 72, wherein the alkylamine is methylamine. Implementation 74. The method of implementation 70, wherein the solvent C) is selected from acetonitrile, dichloroethane, toluene, chlorobenzene, xylene, methanol, ethanol, isopropanol, ethyl acetate, isopropyl acetate, and combinations thereof. Implementation 75. The method of implementation 74, wherein the solvent C) is ethyl acetate. Implementation 76. The method of implementation 70, wherein step II) of the method, which consists of reacting the mixture, occurs at a reaction temperature in the range of approximately 0 °C to approximately 100 °C. Implementation 77. The method of implementation 76, wherein step II) of the method, which consists of reacting the mixture, occurs at a reaction temperature in the range of approximately 20 °C to approximately 30 °C. Implementation 78. The method of implementation 70, wherein the oxidizing agent is selected from oxygen, chlorine, sodium hypochlorite, chromium trioxide, 3-chloroperoxybenzoic acid, hydrogen peroxide, peroxyacetic acid, potassium peroxymonosulfate, potassium permanganate, and combinations thereof. Realization 79. The method of realization 78, wherein the oxidizing agent is hydrogen peroxide. Implementation 80. The method of implementation 70, wherein the solvent c) is selected from acetonitrile, methanol, ethanol, isopropanol, water, dimethylformamide, dimethyl sulfoxide, N-Methylpyrrolidone, tetrahydrofuran, acetic acid, acetic anhydride, propionic acid, butyric acid, and combinations thereof. Realization 81. The method of realization 80, wherein the solvent c) is acetic acid. Realization 82. The method of realization 70, wherein the catalyst is selected from sulfuric acid, hydrogen chloride, nitric acid and combinations thereof. Realization 83. The method of realization 82, wherein the catalyst is sulfuric acid. Implementation 84. The method of implementation 70, wherein step i) of the method, which consists of reacting the mixture, occurs at a reaction temperature in the range of approximately 20 °C to approximately 100 °C. Embodiment 85. The method of embodiment 84, wherein step i) of the method, which consists of reacting the mixture, occurs at a reaction temperature in the range of approximately 60 °C to approximately 65 °C. Embodiment 86. The method of embodiment 70, wherein the compound of Formula IV is prepared according to a method comprising I) form a mixture comprising A) a compound of Formula III, where Rzzcnn / zznz / E / viAi each of Ri - R4 is independently selected from hydrogen, halogen and C1-C5 alkyl; B) a solvent; C) a halogenation reagent; and II) to react the mixture. Implementation 87. The method of implementation 86, wherein the solvent is selected from acetonitrile, dichloroethane, toluene, chlorobenzene, xylene, acetic acid, acetic anhydride, propionic acid, butyric acid, and combinations thereof. Realization 88. The method of realization 87, wherein the solvent is acetic acid. Realization 89. The method of realization 86, wherein the halogenating reagent is selected from a chlorinating reagent, a brominating reagent, an iodinating reagent, and combinations thereof. Implementation 90. The method of implementation 89, wherein the chlorinating reagent is selected from chlorine, thionyl chloride, phosgene, diphosgene, triphosgene, oxalyl chloride, sulfuryl chloride, phosphorus trichloride, phosphorus oxychloride, trichloroisocyanuric acid, and combinations thereof. Realization 91. The method of realization 90, wherein the chlorinating reagent is sulfuryl chloride. Rzzcnn / zznz / E / viAi Implementation 92. The method of implementation 86, wherein step II) of the method, which consists of reacting the mixture, occurs at a reaction temperature in the range of approximately 20 °C to approximately 140 °C. Embodiment 93. The method of embodiment 92, wherein step II) of the method, which consists of reacting the mixture, occurs at a reaction temperature in the range of approximately 120 °C to approximately 130 °C. Embodiment 94. The method of embodiment 86, wherein the compound of Formula III is prepared according to a method comprising I) form a mixture comprising A) a compound of Formula II, where each of Ri - Rs is independently selected from hydrogen, halogen and C1-C5 alkyl; and wherein the compound of Formula II is prepared according to a method comprising i) forming a mixture comprising a) a compound of Formula I, where (Formula I) each of R1 - Rs is independently selected from hydrogen, halogen and C1-C5 alkyl; b) Doral hydrate; c) a hydroxylamine derivative; d) a solvent; e) an inorganic salt; and f) an acid; and i) react the mixture; and B) an acid; and II) to react the mixture. Realization 95. The method of realization 94, wherein acid B) is selected from hydrochloric acid, sulfuric acid, nitric acid, acetic acid, and combinations thereof. Realization 96. The method of realization 95, wherein acid B) is hydrochloric acid. Embodiment 97. The method of embodiment 94, wherein step II) of the method, which consists of reacting the mixture, occurs at a reaction temperature in the range of approximately 10 °C to approximately 90 °C. Embodiment 98. The method of embodiment 97, wherein step II) of the method, which consists of reacting the mixture, occurs at a reaction temperature in the range of approximately 60 °C to approximately 65 °C. Implementation 99. The method of Implementation 94, wherein the hydroxylamine derivative is selected from hydroxylamine sulfate, hydroxylamine hydrochloride, and combinations thereof. Realization 100. The method of realization 99, wherein the hydroxylamine derivative is hydroxylamine sulfate. Realization 101. The method of realization 94, wherein the solvent is selected from methanol, ethanol, toluene, water, and combinations thereof. Realization 102. The method of realization 101, wherein the solvent is water. Realization 103. The method of realization 94, wherein the inorganic salt is selected from sodium sulfate, sodium hydrogen sulfate, sodium chloride, sodium disulfite, potassium sulfate, potassium chloride, and combinations thereof. Realization 104. The method of realization 103, wherein the inorganic salt is sodium sulfate. Realization 105. The method of realization 94, wherein the acid f) is selected from hydrochloric acid, sulfuric acid, nitric acid, hydrobromic acid, formic acid, acetic acid, and combinations thereof. Realization 106. The method of realization 105, wherein the acid f) is hydrochloric acid. Realization 107. The method of realization 94, wherein the concentration of the compound of Formula I in the mixture varies from approximately 1% to approximately 30%. Realization 108. The method of realization 107, wherein the concentration of the compound of Formula I in the mixture is in the range of approximately 3% to approximately 10%. Implementation 109. The method of implementation 94, wherein step i) of the method, which consists of reacting the mixture, occurs at a reaction temperature in the range of approximately 10 °C to approximately 100 °C. Rzzcnn / zznz / E / YiAi Implementation 110. The method of implementation 109, wherein step ii) of the method, which consists of reacting the mixture, occurs at a reaction temperature in the range of approximately 50 °C to approximately 55 °C. Realization 111. The method of realization 70, wherein the compound of Formula IV is prepared according to a method comprising I) form a mixture comprising A) a compound of Formula II, where Rzzcnn / zznz / E / YiAi (Formula II) each of Ri - Rs is independently selected from hydrogen, halogen and C1-C5 alkyl; and B) an acid; II) react the first mixture; III) introduce a halogenation reagent into the first mixture to form a second mixture; IV) react the second mixture. Realization 112. The method of realization 111, wherein the acid is selected from sulfuric acid, acetic acid, and combinations thereof. Realization 113. The method of realization 112, wherein the acid is sulfuric acid. Realization 114. The method of realization 111, wherein the halogenating reagent is selected from a chlorinating reagent, a brominating reagent, an iodinating reagent, and combinations thereof. Implementation 115. The method of implementation 114, wherein the chlorinating reagent is selected from chlorine, thionyl chloride, phosgene, diphosgene, triphosgene, oxalyl chloride, sulfuryl chloride, phosphorus trichloride, phosphorus oxychloride, trichloroisocyanuric acid, and combinations thereof. Realization 116. The method of realization 115, wherein the chlorinating reagent is trichloroisocyanuric acid. Implementation 117. The method of implementation 111, wherein step IV) of the method, which consists of reacting the second mixture, occurs at a reaction temperature in the range of approximately 10 °C to approximately 100 °C. Implementation 118. The method of implementation 117, wherein step IV) of the method, which consists of reacting the second mixture, occurs at a reaction temperature in the range of approximately 10 °C to approximately 65 °C. Embodiment 119. The method of embodiment 111, wherein the compound of Formula II is prepared according to a method comprising i) form a mixture comprising a) a compound of Formula I, where Rzzcnn / zznz / E / YiAi each of Ri - Rs is independently selected from hydrogen, halogen and C1-C5 alkyl; b) Doral hydrate; c) a hydroxylamine derivative; d) a solvent; e) an inorganic salt; and f) an acid; and i) react the mixture. Implementation 120. The method of implementation 119, wherein the hydroxylamine derivative is selected from hydroxylamine sulfate, hydroxylamine hydrochloride, and combinations thereof. Realization 121. The method of realization 120, wherein the hydroxylamine derivative is hydroxylamine sulfate. Realization 122. The method of realization 119, wherein the solvent is selected from methanol, ethanol, toluene, water, and combinations thereof. Realization 123. The method of realization 122, wherein the solvent is water. Realization 124. The method of realization 119, wherein the inorganic salt is selected from sodium sulfate, sodium hydrogen sulfate, sodium chloride, sodium disulfite, potassium sulfate, potassium chloride, and combinations thereof. Realization 125. The method of realization 124, wherein the inorganic salt is sodium sulfate. Realization 126. The method of realization 119, wherein the acid is selected from hydrochloric acid, sulfuric acid, nitric acid, hydrobromic acid, formic acid, acetic acid, and combinations thereof. Realization 127. The method of realization 126, wherein the acid is hydrochloric acid. Implementation 128. The method of implementation 119, wherein the concentration of the compound of Formula I in the mixture varies from approximately 1% to approximately 30%. Realization 129. The method of realization 128, wherein the concentration of the compound of Formula I in the mixture is in the range of approximately 3% to approximately 10%. Implementation 130. The method of implementation 119, wherein the step of the method which consists of reacting the mixture occurs at a reaction temperature in the range of approximately 10 °C to approximately 100 °C. Implementation 131. The method of implementation 130, wherein the step of the method which consists of reacting the mixture occurs at a reaction temperature in the range of approximately 50 °C to approximately 55 °C. Implementation 132. A method for preparing a compound of Formula V, wherein Rzzcnn / zznz / E / YiAi (Formula V) each of R / - R10 is independently selected from hydrogen, halogen, halogenated C1-C5 alkyl and C1-C5 alkyl; and wherein at least one of R7-R10 is a halogen, the method comprising I) form a mixture comprising A) a compound of Formula IV, where (Formula IV) each of R? - Rw is independently selected from hydrogen, halogen, halogenated C1-C5 alkyl and C1-C5 alkyl; and wherein at least one of R7-R10 is a halogen; B) an oxidizing agent; C) a solvent; and D) a catalyst; and II) to react the mixture. Implementation 133. The method of implementation 132, wherein the oxidizing agent is selected from oxygen, chlorine, sodium hypochlorite, chromium trioxide, 3-chloroperoxybenzoic acid, hydrogen peroxide, peroxyacetic acid, potassium peroxymonosulfate, potassium permanganate, and combinations thereof. Realization 134. The method of realization 133, wherein the oxidizing agent is hydrogen peroxide. Implementation 135. The method of implementation 132, wherein the solvent is selected from acetonitrile, methanol, ethanol, isopropanol, water, dimethylformamide, dimethyl sulfoxide, N-Methylpyrrolidone, tetrahydrofuran, acetic acid, acetic anhydride, propionic acid, butyric acid, and combinations thereof. Realization 136. The method of realization 135, wherein the solvent is acetic acid. Implementation 137. The method of implementation 132, wherein the catalyst is selected from sulfuric acid, hydrogen chloride, nitric acid, and combinations thereof. Realization 138. The method of realization 137, wherein the catalyst is sulfuric acid. Implementation 139. The method of implementation 132, wherein step II) of the method, which consists of reacting the mixture, occurs at a reaction temperature in the range of approximately 20 °C to approximately 100 °C. Implementation 140. The method of implementation 139, wherein step II) of the method, which consists of reacting the mixture, occurs at a reaction temperature in the range of approximately 60 °C to approximately 65 °C. Embodiment 141. The method of embodiment 132, wherein the compound of Formula IV is prepared according to a method comprising I) form a mixture comprising A) a compound of Formula III, where Rzzcnn / zznz / E / YiAi each of Ri - R4 is independently selected from hydrogen, halogen and C1-C5 alkyl; B) a solvent; C) a halogenation reagent; and II) to react the mixture. Implementation 142. The method of implementation 141, wherein the solvent is selected from acetonitrile, dichloroethane, toluene, chlorobenzene, xylene, acetic acid, acetic anhydride, propionic acid, butyric acid, and combinations thereof. Realization 143. The method of realization 142, wherein the solvent is acetic acid. Realization 144. The method of realization 141, wherein the halogenating reagent is selected from a chlorinating reagent, a brominating reagent, an iodinating reagent, and combinations thereof. Implementation 145. The method of implementation 144, wherein the chlorinating reagent is selected from chlorine, thionyl chloride, phosgene, diphosgene, triphosgene, oxalyl chloride, sulfuryl chloride, phosphorus trichloride, phosphorus oxychloride, trichloroisocyanuric acid, and combinations thereof. Realization 146. The method of realization 145, wherein the chlorinating reagent is sulfuryl chloride. Implementation 147. The method of implementation 141, wherein step II) of the method, which consists of reacting the mixture, occurs at a reaction temperature in the range of approximately 20 °C to approximately 140 °C. Implementation 148. The method of implementation 147, wherein step II) of the method, which consists of reacting the mixture, occurs at a reaction temperature in the range of approximately 120 °C to approximately 130 °C. Embodiment 149. The method of embodiment 141, wherein the compound of Formula III is prepared according to a method comprising I) form a mixture comprising A) a compound of Formula II, where Rzzcnn / zznz / E / YiAi each of Ri - Rs is independently selected from hydrogen, halogen and C1-C5 alkyl; and wherein the compound of Formula II is prepared according to a method comprising i) forming a mixture comprising a) a compound of Formula I, where (Formula I) each of Ri - Rs is independently selected from hydrogen, halogen and C1-C5 alkyl; b) Doral hydrate; c) a hydroxylamine derivative; d) a solvent; e) an inorganic salt; and f) an acid; and ii) react the mixture; and B) an acid; and II) to react the mixture. Implementation 150. The method of implementation 149, wherein acid B) is selected from hydrochloric acid, sulfuric acid, nitric acid, acetic acid, and combinations thereof. Realization 151. The method of realization 150, wherein acid B) is hydrochloric acid. Implementation 152. The method of implementation 149, wherein step II) of the method, which consists of reacting the mixture, occurs at a reaction temperature in the range of approximately 10 °C to approximately 90 °C. Implementation 153. The method of implementation 152, wherein step II) of the method, which consists of reacting the mixture, occurs at a reaction temperature in the range of approximately 60 °C to approximately 65 °C. Implementation 154. The method of implementation 149, wherein the hydroxylamine derivative is selected from hydroxylamine sulfate, hydroxylamine hydrochloride, and combinations thereof. Implementation 155. The method of implementation 154, wherein the hydroxylamine derivative is hydroxylamine sulfate. Implementation 156. The method of implementation 149, wherein the solvent is selected from methanol, ethanol, toluene, water, and combinations thereof. Realization 157. The method of realization 156, wherein the solvent is water. Implementation 158. The method of implementation 149, wherein the inorganic salt is selected from sodium sulfate, sodium hydrogen sulfate, sodium chloride, sodium disulfite, potassium sulfate, potassium chloride, and combinations thereof. Realization 159. The method of realization 158, wherein the inorganic salt is sodium sulfate. Implementation 160. The method of implementation 149, wherein the acid f) is selected from hydrochloric acid, sulfuric acid, nitric acid, hydrobromic acid, formic acid, acetic acid, and combinations thereof. Realization 161. The method of realization 160, wherein the acid f) is hydrochloric acid. Implementation 162. The method of implementation 149, wherein the concentration of the compound of Formula I in the mixture varies from approximately 1% to approximately 30%. Realization 163. The method of realization 162, wherein the concentration of the compound of Formula I in the mixture is in the range of approximately 3% to approximately 10%. Rzzcnn / zznz / E / viAi Implementation 164. The method of implementation 149, wherein step ii) of the method, which consists of reacting the mixture, occurs at a reaction temperature in the range of approximately 10 °C to approximately 100 °C. Implementation 165. The method of implementation 164, wherein step ii) of the method, which consists of reacting the mixture, occurs at a reaction temperature in the range of approximately 50 °C to approximately 55 °C. Embodiment 166. The method of embodiment 132, wherein the compound of Formula IV is prepared according to a method comprising I) form a mixture comprising A) a compound of Formula II, where R4 Rzzcnn / zznz / E / YiAi (Formula II) each of Ri - Rs is independently selected from hydrogen, halogen and C1-C5 alkyl; and B) an acid; II) react the first mixture; III) introduce a halogenation reagent into the first mixture to form a second mixture; IV) react the second mixture. Realization 167. The method of realization 166, wherein the acid is selected from sulfuric acid, acetic acid, and combinations thereof. Realization 168. The method of realization 167, wherein the acid is sulfuric acid. Realization 169. The method of realization 166, wherein the halogenating reagent is selected from a chlorinating reagent, a brominating reagent, an iodinating reagent, and combinations thereof. Implementation 170. The method of implementation 169, wherein the chlorinating reagent is selected from chlorine, thionyl chloride, phosgene, diphosgene, triphosgene, oxalyl chloride, sulfuryl chloride, phosphorus trichloride, phosphorus oxychloride, trichloroisocyanuric acid, and combinations thereof. Realization 171. The method of realization 170, wherein the chlorinating reagent is trichloroisocyanuric acid. Implementation 172. The method of implementation 166, wherein step IV) of the method, which consists of reacting the second mixture, occurs at a reaction temperature in the range of approximately 10 °C to approximately 100 °C. Implementation 173. The method of implementation 172, wherein step IV) of the method, which consists of reacting the second mixture, occurs at a reaction temperature in the range of approximately 10 °C to approximately 65 °C. Embodiment 174. The method of embodiment 166, wherein the compound of Formula II is prepared 5 according to a method comprising i) forming a mixture comprising a) a compound of Formula I, wherein R110 R2 N H2R3R5r4 (Formula I) each of Ri - Rs is independently selected from hydrogen, halogen and C1-C5 alkyl; b) Doral hydrate; c) a hydroxylamine derivative; d) a solvent; e) an inorganic salt; and f) an acid; and i) react the mixture. Implementation 175. The method of implementation 174, wherein the hydroxylamine derivative is selected from hydroxylamine sulfate, hydroxylamine hydrochloride, and combinations thereof. Realization 176. The method of realization 175, wherein the hydroxylamine derivative is hydroxylamine sulfate. Implementation 177. The method of implementation 174, wherein the solvent is selected from methanol, ethanol, toluene, water, and combinations thereof. Realization 178. The method of realization 177, wherein the solvent is water. 30 Realization 179. The method of realization 174, wherein the inorganic salt is selected from sodium sulfate, sodium hydrogen sulfate, sodium chloride, sodium disulfite, potassium sulfate, potassium chloride, and combinations thereof. Realization 180. The method of realization 179, wherein the inorganic salt is sodium sulfate. Implementation 181. The method of implementation 174, wherein the acid is selected from hydrochloric acid, sulfuric acid, nitric acid, hydrobromic acid, formic acid, acetic acid and combinations thereof. Rzzcnn / zznz / E / viAi of these. Realization 182. The method of realization 181, wherein the acid is hydrochloric acid. Implementation 183. The method of implementation 174, wherein the concentration of the compound of Formula I in the mixture varies from approximately 1% to approximately 30%. Realization 184. The method of realization 183, wherein the concentration of the compound of Formula I in the mixture is in the range of approximately 3% to approximately 10%. Implementation 185. The method of implementation 174, wherein the step of the method which consists of reacting the mixture occurs at a reaction temperature in the range of approximately 10 °C to approximately 100 °C. Implementation 186. The method of implementation 185, wherein the step of the method which consists of reacting the mixture occurs at a reaction temperature in the range of approximately 50 °C to approximately 55 °C. Implementation 187. A method for preparing a compound of Formula IV, wherein Rzzcnn / zznz / E / YiAi (Formula IV) each of R? - Rio is independently selected from hydrogen, halogen, halogenated C1-C5 alkyl and C1-C5 alkyl; wherein at least one of R7-R10 is a halogen, comprising the method I) form a mixture comprising A) a compound of Formula III, where B) a solvent; C) a halogenation reagent; and II) react the mixture. Implementation 188. The method of implementation 187, wherein the solvent is selected from acetonitrile, dichloroethane, toluene, chlorobenzene, xylene, acetic acid, acetic anhydride, propionic acid, butyric acid, and combinations thereof. Realization 189. The method of realization 188, wherein the solvent is acetic acid. Realization 190. The method of realization 187, wherein the halogenating reagent is selected from a chlorinating reagent, a brominating reagent, an iodinating reagent, and combinations thereof. Implementation 191. The method of implementation 190, wherein the chlorinating reagent is selected from chlorine, thionyl chloride, phosgene, diphosgene, triphosgene, oxalyl chloride, sulfuryl chloride, phosphorus trichloride, phosphorus oxychloride, trichloroisocyanuric acid, and combinations thereof. Implementation 192. The method of implementation 191, wherein the chlorinating reagent is chloride of Rzzcnn / zznz / E / YiAi sulphuryl. Implementation 193. The method of implementation 187, wherein step II) of the method, which consists of reacting the mixture, occurs at a reaction temperature in the range of approximately 20 °C to approximately 140 °C. Implementation 194. The method of implementation 193, wherein step II) of the method, which consists of reacting the mixture, occurs at a reaction temperature in the range of approximately 120 °C to approximately 130 °C. Embodiment 195. The method of embodiment 187, wherein the compound of Formula III is prepared according to a method comprising I) form a mixture comprising A) a compound of Formula II, where HN R4 (Formula II) each of Ri - Rs is independently selected from hydrogen, halogen and C1-C5 alkyl; and wherein the compound of Formula II is prepared according to a method comprising i) forming a mixture comprising a) a compound of Formula I, where Ri R2N H2 R3 R5R4 (Formula I) each of R1 - Rs is independently selected from hydrogen, halogen and C1-C5 alkyl; b) Doral hydrate; c) a hydroxylamine derivative; d) a solvent; e) an inorganic salt; and f) an acid; and i) react the mixture; and B) an acid; and II) react the mixture. Implementation 196. The method of implementation 195, wherein acid B) is selected from hydrochloric acid, sulfuric acid, nitric acid, acetic acid, and combinations thereof. Realization 197. The method of realization 196, wherein acid B) is hydrochloric acid. Implementation 198. The method of implementation 195, wherein step II) of the method, which consists of reacting the mixture, occurs at a reaction temperature in the range of approximately 10 °C to approximately 90 °C. Implementation 199. The method of implementation 198, wherein step II) of the method, which consists of reacting the mixture, occurs at a reaction temperature in the range of approximately 60 °C to approximately 65 °C. Implementation 200. The method of implementation 195, wherein the hydroxylamine derivative is selected from hydroxylamine sulfate, hydroxylamine hydrochloride, and combinations thereof. Realization 201. The method of realization 200, wherein the hydroxylamine derivative is hydroxylamine sulfate. Rzzcnn / zznz / E / YiAi Realization 202. The method of realization 195, wherein the solvent is selected from methanol, ethanol, toluene, water, and combinations thereof. Realization 203. The method of realization 202, wherein the solvent is water. Realization 204. The method of realization 195, wherein the inorganic salt is selected from sodium sulfate, sodium hydrogen sulfate, sodium chloride, sodium disulfite, potassium sulfate, potassium chloride, and combinations thereof. Realization 205. The method of realization 204, wherein the inorganic salt is sodium sulfate. Implementation 206. The method of implementation 195, wherein the acid f) is selected from hydrochloric acid, sulfuric acid, nitric acid, hydrobromic acid, formic acid, acetic acid, and combinations thereof. Rzzcnn / zznz / E / viAi Realization 207. The method of realization 206, wherein the acid f) is hydrochloric acid. Realization 208. The method of realization 195, wherein the concentration of the compound of Formula I in the mixture varies from approximately 1% to approximately 30%. Implementation 209. The method of Implementation 208, wherein the concentration of the compound of Formula I in the mixture is in the range of approximately 3% to approximately 10%. Implementation 210. The method of implementation 195, wherein step ii) of the method, which consists of reacting the mixture, occurs at a reaction temperature in the range of approximately 10 °C to approximately 100 °C. Embodiment 211. The method of embodiment 210, wherein step i) of the method, which consists of reacting the mixture, occurs at a reaction temperature in the range of approximately 50 °C to approximately 55 °C. Implementation 212. A method for preparing a compound of Formula III, wherein Each of Ri - R4 is independently selected from hydrogen, halogen, and C1-C5 alkyl, comprising the method I) form a mixture comprising A) a compound of Formula II, where OH (Formula II) each of R1 - Rs is independently selected from hydrogen, halogen and C1-C5 alkyl; and wherein the compound of Formula II is prepared according to a method comprising i) forming a mixture comprising a) a compound of Formula I, where Rzzcnn / zznz / E / YiAi each of Ri - Rs is independently selected from hydrogen, halogen and C1-C5 alkyl; b) Doral hydrate; c) a hydroxylamine derivative; d) a solvent; e) an inorganic salt; and f) an acid; and i) react the mixture; and B) an acid; and II) react the mixture. Realization 213. The method of realization 212, wherein acid B) is selected from hydrochloric acid, sulfuric acid, nitric acid, acetic acid, and combinations thereof. Realization 214. The method of realization 213, wherein acid B) is hydrochloric acid. Implementation 215. The method of implementation 212, wherein step II) of the method, which consists of reacting the mixture, occurs at a reaction temperature in the range of approximately 10 °C to approximately 90 °C. Implementation 216. The method of implementation 215, wherein step II) of the method, which consists of reacting the mixture, occurs at a reaction temperature in the range of approximately 60 °C to approximately 65 °C. Implementation 217. The method of implementation 212, wherein the hydroxylamine derivative is selected from hydroxylamine sulfate, hydroxylamine hydrochloride, and combinations thereof. Realization 218. The method of realization 217, wherein the hydroxylamine derivative is hydroxylamine sulfate. Implementation 219. The method of implementation 212, wherein the solvent is selected from methanol, ethanol, toluene, water, and combinations thereof. Realization 220. The method of realization 219, wherein the solvent is water. Realization 221. The method of realization 212, wherein the inorganic salt is selected from sodium sulfate, sodium hydrogen sulfate, sodium chloride, sodium disulfite, potassium sulfate, potassium chloride, and combinations thereof. Realization 222. The method of realization 221, wherein the inorganic salt is sodium sulfate. Implementation 223. The method of implementation 212, wherein the acid f) is selected from hydrochloric acid, sulfuric acid, nitric acid, hydrobromic acid, formic acid, acetic acid, and combinations thereof. Rzzcnn / zznz / E / viAi Realization 224. The method of realization 223, wherein the acid f) is hydrochloric acid. Realization 225. The method of realization 212, wherein the concentration of the compound of Formula I in the mixture varies from approximately 1% to approximately 30%. Realization 226. The method of realization 225, wherein the concentration of the compound of Formula I in the mixture is in the range of approximately 3% to approximately 10%. Implementation 227. The method of implementation 212, wherein step i) of the method, which consists of reacting the mixture, occurs at a reaction temperature in the range of approximately 10 °C to approximately 100 °C. Embodiment 228. The method of embodiment 227, wherein step i) of the method, which consists of reacting the mixture, occurs at a reaction temperature in the range of approximately 50 °C to approximately 55 °C. Implementation 229. A method for preparing a compound of Formula II, wherein (Formula II) each of Ri - Rs is independently selected from hydrogen, halogen and C1-C5 alkyl, comprising the method I) form a mixture comprising A) a compound of Formula I, where (Formula I) each of R1 - Rs is independently selected from hydrogen, halogen and C1-C5 alkyl; B) Doral hydrate; C) a hydroxylamine derivative; D) a solvent; E) an inorganic salt; and F) an acid; and II) to react the mixture. Implementation 230. The method of implementation 229, wherein the hydroxylamine derivative is selected from hydroxylamine sulfate, hydroxylamine hydrochloride, and combinations thereof. Realization 231. The method of realization 230, wherein the hydroxylamine derivative is hydroxylamine sulfate. Implementation 232. The method of implementation 229, wherein the solvent is selected from methanol, ethanol, toluene, water, and combinations thereof. Realization 233. The method of realization 232, wherein the solvent is water. Realization 234. The method of realization 229, wherein the inorganic salt is selected from sodium sulfate, sodium hydrogen sulfate, sodium chloride, sodium disulfite, potassium sulfate, potassium chloride, and combinations thereof. Realization 235. The method of realization 234, wherein the inorganic salt is sodium sulfate. Realization 236. The method of realization 229, wherein the acid is selected from hydrochloric acid, sulfuric acid, nitric acid, hydrobromic acid, formic acid, acetic acid, and combinations thereof. Realization 237. The method of realization 236, wherein the acid is hydrochloric acid. Implementation 238. The method of implementation 229, wherein the concentration of the compound of Formula I in the mixture varies from approximately 1% to approximately 30%. Realization 239. The method of realization 238, wherein the concentration of the compound of Formula I in the mixture is in the range of approximately 3% to approximately 10%. Embodiment 240. The method of embodiment 229, wherein the step of the method which consists of reacting the mixture occurs at a reaction temperature in the range of approximately 10 °C to approximately 100 °C. Embodiment 241. The method of embodiment 240, wherein the step of the method which consists of reacting the mixture occurs at a reaction temperature in the range of approximately 50 °C to approximately 55 °C. Implementation 242. A method for preparing a compound of Formula IV, wherein Rzzcnn / zznz / E / YiAi (Formula IV) each of R? - Rio is independently selected from hydrogen, halogen, halogenated C1-C5 alkyl and C1-C5 alkyl; wherein at least one of R7-R10 is a halogen, comprising the method I) form a first mixture comprising A) a compound of Formula II, where Rzzcnn / zznz / E / viAi (Formula II) each of R1 - R5 is independently selected from hydrogen, halogen and C1-C5 alkyl; and B) an acid; II) react the first mixture; III) introduce a halogenation reagent into the first mixture to form a second mixture; IV) react the second mixture. Realization 243. The method of realization 242, wherein the acid is selected from sulfuric acid, acetic acid, and combinations thereof. Realization 244. The method of realization 243, wherein the acid is sulfuric acid. Implementation 245. The method of implementation 242, wherein the halogenating reagent is selected from a chlorinating reagent, a brominating reagent, an iodinating reagent, and combinations thereof. Implementation 246. The method of implementation 245, wherein the chlorinating reagent is selected from chlorine, thionyl chloride, phosgene, diphosgene, triphosgene, oxalyl chloride, sulfuryl chloride, phosphorus trichloride, phosphorus oxychloride, trichloroisocyanuric acid, and combinations thereof. Realization 247. The method of realization 246, wherein the chlorinating reagent is trichloroisocyanuric acid. Implementation 248. The method of implementation 242, wherein step IV) of the method, which consists of reacting the second mixture, occurs at a reaction temperature in the range of approximately 10 °C to approximately 100 °C. Embodiment 249. The method of embodiment 248, wherein step IV) of the method, which consists of reacting the second mixture, occurs at a reaction temperature in the range of approximately 10 °C to approximately 65 °C. Embodiment 250. The method of embodiment 242, wherein the compound of Formula II is prepared according to a method comprising i) form a mixture comprising a) a compound of Formula I, where Rzzcnn / zznz / E / YiAi each of Ri - Rs is independently selected from hydrogen, halogen and C1-C5 alkyl; b) Doral hydrate; c) a hydroxylamine derivative; d) a solvent; e) an inorganic salt; f) an acid; and i) react the mixture. Implementation 251. The method of implementation 250, wherein the hydroxylamine derivative is selected from hydroxylamine sulfate, hydroxylamine hydrochloride, and combinations thereof. Implementation 252. The method of implementation 251, wherein the hydroxylamine derivative is hydroxylamine sulfate. Implementation 253. The method of implementation 250, wherein the solvent is selected from methanol, ethanol, toluene, water, and combinations thereof. Realization 254. The method of realization 253, wherein the solvent is water. Realization 255. The method of realization 250, wherein the inorganic salt is selected from sodium sulfate, sodium hydrogen sulfate, sodium chloride, sodium disulfite, potassium sulfate, potassium chloride, and combinations thereof. Realization 256. The method of realization 255, wherein the inorganic salt is sodium sulfate. Realization 257. The method of realization 250, wherein the acid is selected from hydrochloric acid, sulfuric acid, nitric acid, hydrobromic acid, formic acid, acetic acid, and combinations thereof. Realization 258. The method of realization 257, wherein the acid is hydrochloric acid. Implementation 259. The method of implementation 250, wherein the concentration of the compound of Formula I in the mixture varies from approximately 1% to approximately 30%. Realization 260. The method of realization 259, wherein the concentration of the compound of Formula I in the mixture is in the range of approximately 3% to approximately 10%. Implementation 261. The method of implementation 250, wherein the step of the method which consists of reacting the mixture occurs at a reaction temperature in the range of approximately °C to approximately 100 °C. Embodiment 262. The method of embodiment 261, wherein the step of the method which consists of reacting the mixture occurs at a reaction temperature in the range of approximately 50 °C to approximately 55 °C. In one aspect, a compound of Formula VI is prepared according to a method represented by Scheme 1. The R groups are as defined anywhere in this disclosure. SCHEME 1. (I) (II) (III) (V) (VI) Rzzcnn / zznz / E / YiAi In one aspect, a compound of Formula VI is prepared according to a method represented by Scheme 2. The R groups are as defined anywhere in this disclosure. SCHEME 2. R10O <v>(VI) In one aspect, a compound of Formula VI is prepared according to a method represented by Scheme 3. The R groups are as defined anywhere in this disclosure. SCHEME 3. (Vi) In one aspect, 2-amino-5-chloro-N,3-dimethylbenzamide is prepared according to a method represented by Scheme 4. SCHEME 4. In one aspect, 2-amino-5-chloro-N,3-dimethylbenzamide is prepared according to a method represented by Scheme 5. SCHEME 5. In one aspect, 2-amino-5-chloro-N,3-dimethylbenzamide is prepared according to a method represented by Scheme 6. SCHEME 6. Azzcnn / zznz / E / YiAi In one respect, a compound of Formula II is prepared according to a method represented by Scheme 7. The R groups are as defined anywhere in this disclosure. SCHEME 7. This aspect includes reacting a compound of Formula I with doral hydrate and hydroxylamine sulfate in a solvent at a reaction concentration in the presence of an inorganic salt and an acid. In one embodiment, the compound of Formula I is toluidine. In one embodiment, the solvent is selected from MeOH, EtOH, toluene, water, and combinations thereof. In another embodiment, the solvent is water. In one embodiment, the inorganic salt is selected from sodium sulfate, sodium hydrogen sulfate, sodium chloride, sodium disulfite, potassium sulfate, potassium chloride, and combinations thereof. In another embodiment, the inorganic salt is sodium sulfate. In one embodiment, the acid is selected from hydrogen chloride, sulfuric acid, nitric acid, hydrobromic acid, formic acid, acetic acid, and combinations thereof. In another embodiment, the acid is hydrogen chloride.In one embodiment, the reaction concentration is in the range of approximately 1% to approximately 30% for the compound of Formula I. In another embodiment, the reaction concentration is in the range of approximately 3% to approximately 10% for the compound of Formula I. In one embodiment, the reaction temperature is in the range of approximately 10°C to approximately 100°C. In another embodiment, the reaction temperature is in the range of approximately 50°C to approximately 55°C. When the reaction conditions of a reaction temperature of 90 °C in water are applied to a compound of Formula I, where the compound of Formula I is toluidine, (E)-2-(hydroxyimino)-N-(o-tolyl)acetamide is obtained as a sticky solid, leading to difficult and poor separation. Furthermore, rapid temperature increases occur when this crude (E)-2-(hydroxyimino)-N-(o-tolyl)acetamide is added in portions in subsequent reaction steps. This problem is overcome in the present disclosure by lowering the reaction temperature in water from 90 °C to a temperature in the range of approximately 50 to approximately 55 °C. This change not only results in pure (E)2-(hydroxyimino)-N-(o-tolyl)acetamide with a good morphotype but also advantageously increases the reaction concentration. This higher reaction concentration reduces wastewater and costs. In one respect, a compound of Formula III is prepared according to a method represented by Scheme 8. The R groups are as defined anywhere in this disclosure. SCHEME 8. Rzzcnn / zznz / E / YiAi This aspect includes reacting a compound of Formula II with an acid that is also used as a solvent. In one embodiment, the acid is selected from hydrochloric acid, sulfuric acid, nitric acid, acetic acid, and combinations thereof. In another embodiment, the acid is sulfuric acid. In one embodiment, the reaction temperature is in the range of approximately 10°C to approximately 90°C. In another embodiment, the reaction temperature is in the range of approximately 60°C to 65°C. In one aspect, a compound of Formula IV is prepared according to a method represented by Scheme 9. The R groups are as defined anywhere in this disclosure. SCHEME 9. R1R or IHr I HR2\^k^NR8\ / k^N J ---* Jj0° R OR OK4«10 (IP)(IV) This aspect includes reacting a compound of Formula III with a halogenating reagent in a solvent. In one embodiment, the halogenating reagent is selected from fluorinating agents, chlorinating agents, brominating agents, iodinating agents, and combinations thereof. In one embodiment, the halogenating reagent is a chlorinating reagent selected from chlorine, thionyl chloride, phosgene, diphosgene, triphosgene, oxalyl chloride, sulfuryl chloride, phosphorus trichloride, phosphorus oxychloride, trichloroisocyanuric acid, and combinations thereof. In another embodiment, the chlorinating reagent is sulfuryl chloride. In one embodiment, the solvent is selected from acetonitrile (ACN), 1,2-dichloroethane (DCE), toluene, chlorobenzene, xylene, acetic acid, acetic anhydride, propionic acid, butyric acid, and combinations thereof. In another embodiment, the solvent is acetic acid.In one embodiment, the reaction temperature is in the range of approximately 20 °C to approximately 140 °C. In another embodiment, the reaction temperature is in the range of approximately 120 °C to approximately 130 °C. In one aspect, a compound of Formula IV is prepared according to a method represented by Scheme 10. The R groups are as defined anywhere in this disclosure. SCHEME 10. R4(Π) (IV) Azzcnn / zznz / E / YiAi This aspect includes reacting, in a first reaction, a compound of Formula II with an acid that is also used as a solvent, then adding a halogenating agent, and, in a second reaction, forming a compound of Formula IV. In one embodiment, the acid is selected from acetic acid, sulfuric acid, and combinations thereof. In another embodiment, the acid is sulfuric acid. In one embodiment, the halogenating agent is selected from fluorinating agents, chlorinating agents, brominating agents, iodinating agents, and combinations thereof. In one embodiment, the halogenating agent is a chlorinating agent selected from chlorine, thionyl chloride, phosgene, diphosgene, triphosgene, oxalyl chloride, sulfuryl chloride, phosphorus trichloride, phosphorus oxychloride, trichloroisocyanuric acid, and combinations thereof. In another embodiment, the chlorinating agent is trichloroisocyanuric acid.In one embodiment, the reaction temperature of the first reaction is in the range of approximately 0 °C to approximately 100 °C. In another embodiment, the reaction temperature of the first reaction is in the range of approximately 10 °C to approximately 65 °C. In one embodiment, the reaction temperature of the second reaction is in the range of approximately 10 °C to approximately 100 °C. In another embodiment, the reaction temperature of the second reaction is in the range of approximately 10 °C to 65 °C. This aspect is a single-vessel process and offers several advantages. First, it eliminates the need to separate intermediates produced from the Formula II compound, such as the Formula III compound, before subsequent reactions. Second, it reduces potential losses of intermediates produced from the Formula II compound, such as the Formula III compound. Third, it increases the overall yield. Fourth, it reduces the number of reaction steps and post-treatment operations. Fifth, it reduces the overall cost. In one aspect, a compound of Formula V is prepared according to a method represented by Scheme 11. The R groups are as defined anywhere in this disclosure. SCHEME 11. (IV) (V) This aspect includes adding an oxidizing agent to an aqueous solution containing a compound of Formula IV in the presence of catalysis. In one embodiment, the oxidizing agent is selected from oxygen, chlorine, sodium hypochlorite, chromium trioxide, 3-chloroperoxybenzoic acid, hydrogen peroxide, peroxyacetic acid, potassium peroxymonosulfate, potassium permanganate, and combinations thereof. In another embodiment, the oxidizing agent is hydrogen peroxide. In one embodiment, the solvent is selected from acetonitrile (ACN), methanol (MeOH), ethanol (EtOH), isopropyl alcohol (7-PrOH), water (H₂O), dimethylformamide (DMF), dimethyl sulfoxide (DMSO), N-methyl-2-pyrrolidone (NMP), tetrahydrofuran (THF), acetic acid, acetic anhydride, propionic acid, butyric acid, and combinations thereof. In another embodiment, the solvent is acetic acid. In one embodiment, the catalyst is selected from sulfuric acid, hydrogen chloride, nitric acid, and combinations thereof.In another embodiment, the catalyst is sulfuric acid. In one embodiment, the reaction temperature is in the range of approximately 20 °C to approximately 100 °C. In another embodiment, the reaction temperature is in the range of approximately 60 °C to approximately 65 °C. In one aspect, a compound of Formula VI is prepared according to a method represented by Scheme 12. The R groups are as defined anywhere in this disclosure. SCHEME 12. Rzzcnn / zznz / E / viAi (VI) This aspect includes reacting a compound of Formula V with an alkylamine in a solvent. In one embodiment, the alkylamine comprises a functional group selected from branched C1Cw alkyl and unbranched C1-C10 alkyl. In another embodiment, the alkylamine is selected from methylamine, ethylamine, propylamine, isopropylamine, butylamine, f-butylamine, and combinations thereof. In one embodiment, the solvent is selected from acetonitrile (ACN), 1,2-dichloroethane (DCE), toluene, chlorobenzene, xylene, methanol (MeOH), ethanol (EtOH), isopropyl alcohol (β-PrOH), ethyl acetate (EtOAc), isopropyl acetate (IPAc), and combinations thereof. In another embodiment, the solvent is EtOAc. In one embodiment, the reaction temperature is in the range of approximately 0 °C to approximately 100 °C. In another embodiment, the reaction temperature is in the range of approximately 20 °C to approximately 30 °C. In one aspect, a compound of Formula V is prepared according to a method represented by Scheme 13. The R groups are as defined anywhere in this disclosure. SCHEME 13. r7 River (V) Rzzcnn / zznz / E / YiAi of Formula III with a reagent of This aspect includes reacting a halogenating compound in a solvent and then adding an oxidizing agent to the solution in the presence of a catalyst. In one embodiment, the halogenating reagent is selected from fluorinating agents, chlorinating agents, brominating agents, iodinating agents, and combinations thereof. In another embodiment, the halogenating reagent is a chlorinating agent selected from chlorine, thionyl chloride, phosgene, diphosgene, triphosgene, oxalyl chloride, sulfuryl chloride, phosphorus trichloride, phosphorus oxychloride, trichloroisocyanuric acid, and combinations thereof. In yet another embodiment, the halogenating reagent is sulfuryl chloride. In one embodiment, the solvent is selected from ACN, DCE, toluene, chlorobenzene, xylene, acetic acid, acetic anhydride, propionic acid, and butyric acid. In another embodiment, the solvent is acetic acid.In one embodiment, the reaction temperature for halogenation is in the range of approximately 20 °C to approximately 140 °C. In another embodiment, the reaction temperature for halogenation is in the range of approximately 120 °C to approximately 130 °C. In one embodiment, the oxidizing agent is selected from oxygen, chlorine, sodium hypochlorite, chromium trioxide, 3-chloroperoxybenzoic acid, hydrogen peroxide, peroxyacetic acid, potassium peroxymonosulfate, potassium permanganate, and combinations thereof. In another embodiment, the oxidizing agent is hydrogen peroxide. In one embodiment, the catalyst is selected from sulfuric acid, hydrogen chloride, nitric acid, potassium hydroxide, and combinations thereof. In another embodiment, the catalyst is sulfuric acid. In one embodiment, the reaction temperature for oxidation is in the range of approximately 20 °C to approximately 100 °C.In another embodiment, the reaction temperature for the oxidation is in the range of approximately 60 °C to approximately 65 °C. This aspect is a single-vessel process and offers several advantages. First, it eliminates the need to separate intermediates produced from the Formula III compound, such as the Formula IV compound, before subsequent reactions. Second, it reduces potential losses of intermediates produced from the Formula III compound, such as the Formula IV compound. Third, it increases the overall yield. Fourth, it reduces the number of reaction steps and post-treatment operations. Fifth, it reduces the overall cost. EXAMPLES Without going into further detail, it is believed that a person skilled in the art using the foregoing description can derive the full benefit from the present invention. Therefore, the following Examples are to be interpreted as merely illustrative and not limiting disclosure in any way. The starting material for the following Examples may not necessarily have been prepared by a particular preparation process described in other Examples. It is also understood that any numerical range mentioned herein includes all values ​​from the lowest to the highest. For example, if a range is stated as 10-50, it is intended that values ​​such as 12-30, 20-40, or 30-50, etc., are expressly listed in this specification.These are only examples of what is specifically intended, and it should be considered that all possible combinations of numerical values ​​between the lowest and highest values ​​listed, both inclusive, are expressly indicated in this application. EXAMPLE 1. REACTION OF O-TOLUIDINE 11.5 g of o-toluidine, 12.0 g of hydrochloric acid, 19.7 g of doral hydrate, 27.0 g of hydroxylamine sulfate, 30.0 g of sodium sulfate, and 200.0 g of water were introduced into a reactor. The reaction temperature was controlled at 55–60 °C. After the reaction, the mixture was cooled to room temperature and filtered. The material retained on the filter was washed with water and dried. 13.2 g of high-purity (E)-3-hydroxy-N-(o-tolyl)acrylamide were obtained. EXAMPLE 2. CYCLIZATION. Twenty.0 g of (E)-3-hydroxy-N-(o-tolyl)acrylamide were added in portions, to control the reaction temperature, to sulfuric acid in a reactor. The reaction temperature was controlled between 60 °C and 65 °C. After the reaction, the mixture was cooled to room temperature and added to ice water. The mixture was stirred and filtered. The material retained on the filter was washed with water and dried. Sixteen.0 g of 7-methylindolin-2,3-dione were obtained. This crude product could be used for further reactions without additional processing. EXAMPLE 3. HALOGENATION. 30.0 g of 7-methylindolin-2,3-dione, 50.3 g of sulfuryl chloride, and 100.0 g of acetic acid were introduced into a reactor. The reaction temperature was controlled at 120–125 °C. After the reaction, the mixture was cooled to room temperature. Water was added to the mixture, which was stirred at room temperature. The mixture was filtered. The material retained on the filter was washed with water and dried. 29.1 g of 5-chloro-7-methylindolin-2,3-dione were obtained. EXAMPLE 4. OXIDATION 18.0 g of 5-chloro-7-methylindolin-2,3-dione, 100.0 g of acetic acid, and 1.0 g of sulfuric acid were introduced into a reactor. The reaction temperature was controlled at 60–65 °C. At this temperature, 13.0 g of 30% hydrogen peroxide solution was added dropwise to maintain the temperature between 60–65 °C. After the reaction, water was added to the mixture, which was stirred at room temperature. The mixture was filtered. The material retained on the filter was washed with water and dried. 14.6 g of 6-chloro-8-methyl-2H-benzo[d][1,3]oxazin-2,4(1H)-dione were obtained. EXAMPLE 5. REACTION WITH METHANAMINE 10.0 g of 6-chloro-8-methyl-2H-benzo[d][1,3]oxazin-2,4(1H)-dione and 100.0 g of ethyl acetate were introduced into a reactor. Gaseous methanamine was bubbled into the reaction at room temperature. Rzzcnn / zznz / E / YiAi After the reaction, the mixture was extracted with water. The solvent was removed from the organic phase under vacuum. 8.5 g of crude 2-amino-5-chloro-N,3-dimethylbenzamide product were obtained. EXAMPLE 6. SYNTHESIS IN A SINGLE CONTAINER 30.0 g of 7-methylindoline-2,3-dione, 50.3 g of sulfuryl chloride, and 164.0 g of acetic acid were introduced into a reactor. The reaction temperature was controlled at 120–125 °C. Once the 7-methylindoline-2,3-dione was consumed, the reaction temperature was cooled to 60–65 °C. 41.4 g of 30% hydrogen peroxide solution were added dropwise to maintain the temperature between 60–65 °C. After the reaction, water was added to the mixture, which was stirred at room temperature. The mixture was filtered. The material retained on the filter was washed with water and dried. 27.6 g of 6-chloro-8-methyl-2Hbenzo[d][1,3]oxazin-2,4(1 H)-dione were obtained. This written description uses examples to illustrate the present disclosure, including the best manner, and also to enable any person skilled in the art to put the disclosure into practice, including the preparation and use of any devices or systems and the performance of any methods incorporated therein. The patentable scope of the disclosure is defined by the claims and may include other examples that occur to those skilled in the art. Such other examples are intended to be within the scope of the claims if they have structural elements that do not differ from the literal language of the claims or if they include equivalent structural elements with insubstantial differences from the literal language of the claims.< / v>

Claims

1. A method for preparing a compound of Formula VI, wherein Rzzcnn / zznz / E / YiAi R11 (Formula VI) each of R7 - Rw is independently selected from hydrogen, halogen, halogenated C1-C5 alkyl and C1-C5 alkyl; wherein at least one of R7-R10 is a halogen; and wherein Rn is selected from branched C1-C10 alkyl and unbranched C1-C10 alkyl, the method comprising I) forming a mixture comprising A) a compound of Formula V, wherein (Formula V) each of R7 - R10 is independently selected from hydrogen, halogen, halogenated C1-C5 alkyl and C1-C5 alkyl; wherein at least one of R7-R10 is a halogen; and wherein the compound of Formula V is prepared according to a method comprising i) forming a first mixture comprising a) a compound of Formula III, wherein Rzzcnn / zznz / E / viAi each of Ri - R4 is independently selected from hydrogen, halogen and C1-C5 alkyl; b) a solvent; and c) a halogenating reagent;ii) reacting the first mixture; iii) introducing a second mixture into the first mixture to form a third mixture, the second mixture comprising d) an oxidizing agent; e) a catalyst; and iv) reacting the third mixture; B) an alkylamine; and C) a solvent; and II) reacting the mixture.

2. The method of claim 1, wherein the alkylamine comprises a functional group selected from branched C1-C10 alkyl and unbranched C1-C10 alkyl.

3. The method of claim 1, wherein the solvent C) is selected from acetonitrile, dichloroethane, toluene, chlorobenzene, xylene, methanol, ethanol, isopropanol, ethyl acetate, isopropyl acetate and combinations thereof.

4. The method of claim 1, wherein step II) of the method, which consists of reacting the mixture, occurs at a reaction temperature in the range of approximately 0 °C to approximately 100 °C.

5. The method of claim 1, wherein the solvent b) is selected from acetonitrile, dichloroethane, toluene, chlorobenzene, xylene, acetic acid, acetic anhydride, propionic acid, butyric acid and combinations thereof.

6. The method of claim 1, wherein the halogenation reagent is selected from a chlorination reagent, a bromination reagent, an iodination reagent, and combinations thereof.

7. The method of claim 1, wherein step i) of the method, which consists of reacting the first mixture, occurs at a reaction temperature in the range of approximately 20 °C to approximately 140 °C.

8. The method of claim 1, wherein the oxidizing agent is selected from oxygen, chlorine, sodium hypochlorite, chromium trioxide, 3-chloroperoxybenzoic acid, hydrogen peroxide, peroxyacetic acid, potassium peroxymonosulfate, potassium permanganate, and combinations thereof.

9. The method of claim 1, wherein the catalyst is selected from sulfuric acid, hydrogen chloride, nitric acid, and combinations thereof. > s 51ii c N 10. The method of claim 1, wherein step iv) of the method, which consists of reacting the third mixture, occurs at a reaction temperature in the range of approximately 20 °C to approximately 100 °C.

11. The method of claim 1, wherein the compound of Formula III is prepared according to a method comprising I) forming a mixture comprising A) a compound of Formula II, wherein (Formula II) each of Ri - Rs is independently selected from hydrogen, halogen, and C1-C5 alkyl; and wherein the compound of Formula II is prepared according to a method comprising i) forming a mixture comprising a) a compound of Formula I, wherein (Formula I) each of R1 - R5 is independently selected from hydrogen, halogen, and C1-C5 alkyl; b) doral hydrate; c) a hydroxylamine derivative; d) a solvent; e) an inorganic salt; and f) an acid; and i) reacting the mixture; and B) an acid; and II) reacting the mixture. 12.A method for preparing a compound of Formula V, wherein each of R7-R10 is independently selected from hydrogen, halogen, halogenated C1-C5 alkyl, and C1-C5 alkyl; and wherein at least one of R7-R10 is a halogen, the method comprising: I) forming a first mixture comprising A) a compound of Formula III, wherein each of R1-R4 is independently selected from hydrogen, halogen, and C1-C5 alkyl; B) a solvent; and C) a halogenating reagent; II) reacting the first mixture; III) introducing a second mixture into the first mixture to form a third mixture, the second mixture comprising D) an oxidizing agent; and E) a catalyst; and IV) reacting the third mixture.

13. A method for preparing a compound of Formula VI, wherein (Formula VI) each of R7 - R10 is independently selected from hydrogen, halogen, halogenated C1-C5 alkyl and C1-C5 alkyl; wherein at least one of R7-R10 is a halogen; and wherein Rn is selected from branched C1-C10 alkyl and unbranched C1-C10 alkyl, the method comprising I) forming a mixture comprising A) a compound of Formula V, wherein (Formula V) each of R7 - R10 is independently selected from hydrogen, halogen, halogenated C1-C5 alkyl and C1-C5 alkyl; wherein at least one of R7-R10 is a halogen; and wherein the compound of Formula V is prepared according to a method comprising i) forming a mixture comprising a) a compound of Formula IV, wherein (Formula IV) each of R? - Rio is independently selected from hydrogen, halogen, halogenated C1-C5 alkyl and C1-C5 alkyl; and wherein at least one of R7-R10 is a halogen;b) an oxidizing agent; c) a solvent; and d) a catalyst; and ii) react the mixture; B) an alkylamine; and C) a solvent; and II) react the mixture.

14. The method of claim 13, wherein the alkylamine comprises a functional group selected from branched C1-C10 alkyl and unbranched C1-C10 alkyl.

15. The method of claim 13, wherein the solvent C) is selected from acetonitrile, dichloroethane, toluene, chlorobenzene, xylene, methanol, ethanol, isopropanol, ethyl acetate, isopropyl acetate, and combinations thereof.

16. The method of claim 13, wherein step II) of the method, which consists of reacting the mixture, occurs at a reaction temperature in the range of approximately 0 °C to approximately 100 °C.

17. The method of claim 13, wherein the oxidizing agent is selected from oxygen, chlorine, sodium hypochlorite, chromium trioxide, 3-chloroperoxybenzoic acid, hydrogen peroxide, peroxyacetic acid, potassium peroxymonosulfate, potassium permanganate, and combinations thereof.

18. The method of claim 13, wherein the catalyst is selected from sulfuric acid, hydrogen chloride, nitric acid, and combinations thereof.

19. A method for preparing a compound of Formula IV, wherein Rzzcnn / zznz / E / YiAi each of R7 - R10 is independently selected from hydrogen, halogen, halogenated C1-C5 alkyl and C1-C5 alkyl; wherein at least one of R7-R10 is a halogen, the method comprising I) forming a mixture comprising A) a compound of Formula III, wherein Rzzcnn / zznz / E / YiAi each of Ri - R4 is independently selected from hydrogen, halogen and C1-C5 alkyl; B) a solvent; C) a halogenating reagent; and II) reacting the mixture.

20. The method of claim 19, wherein the solvent is selected from acetonitrile, dichloroethane, toluene, chlorobenzene, xylene, acetic acid, acetic anhydride, propionic acid, butyric acid and combinations thereof.