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Synthesis of pyrazolinylnaphthalic acid derivatives

a technology of pyrazolinylnaphthalic acid and derivatives, which is applied in the field of synthesis of pyrazolinylnaphthalic acid derivatives, can solve the problems of increasing production costs, low product containing considerable amounts of impurities, so as to enhance the yield and quality of final products, simplify the process, and reduce the time it takes to synthesize

Inactive Publication Date: 2001-08-09
EMAGIN CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0035] It is another object of the present invention to provide a method to simplify and reduce the time it takes to synthesize the above compounds.
[0036] It is a further object of the present invention to enhance the final product yield and quality (purity grade) of the above compounds.

Problems solved by technology

(A) Low quality of the final product.
The product contains considerable amounts of impurities, mainly unsaturated naphthalic acid derivatives that cause green fluorescence.
The final product purification from the impurities mentioned is associated with difficulties in the process, increased production costs, and substantial losses of the final product.
To obtain high-quality luminophors, the chromatographic purification is required resulting in a loss of 30 to 40% of the final product.
(B) The process is difficult to perform and laborious.
These preparations make the process difficult and increase its cost.
(C) Moreover, the process is complicated by the purification of intermediates both at the stages of their synthesis and at the preparation of final products.

Method used

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  • Synthesis of pyrazolinylnaphthalic acid derivatives
  • Synthesis of pyrazolinylnaphthalic acid derivatives
  • Synthesis of pyrazolinylnaphthalic acid derivatives

Examples

Experimental program
Comparison scheme
Effect test

example 1

Production of 4-(1,5-diphenyl-2-pyrasolinyl-3)-N-phenylnaphtalimide

[0126] A mixture of 10.8 g of 4-acetylnaphtalic anhydride (obtained by the acetylation of acenaphtene with acetic anhydride in the presence of anhydrous zinc chloride and by the oxidation of the formed acetylnaphtene with sodium dichromate), 5.3 g of benzaldehyde, and 120 ml of 4.4% caustic soda solution is stirred at room temperature for 3 hours. The precipitate--disodium salt of 4-cinnamoylnaphtalic acid--is separated by filtering and washed with alcohol.

[0127] A mixture of 15.79 g of disodium salt of 4-cinnamoylnaphtalic acid, 4.89 g of aniline and 60 ml of acetic acid is boiled for 6 hours. The reaction mixture is then allowed to cool down to room temperature (20.degree. C.). The formed precipitate is separated by filtering and washed on the filter with water and hot alcohol.

[0128] A mixture of 12.1 g of 4-cinnamoyl-N-naphtalimide, 4.26 g of phenylhydrazine, 100 ml of ethyl alcohol and 6 ml of 10% alkaline soluti...

example 2

Production of 4-[1-phenyl-5-(4-methoxyphenyl)-2-pyrazolinyl-3)-N-phenylnap-htalimide

[0130] This compound is produced and cleaned as the product in example 1. The source products are 4-acetylnaphalic anhydride (10.8 g), anisic aldehyde (6.12 g), aniline (4.89 g), and phenylhydrazine (4.1 g).

[0131] The end product is made up of dark red crystals; it is soluble in common organic solvents and water-insoluble. The melting temperature is 215.degree. C. The yield is 12.13 g (80%).

[0132] .sub.max. lum. in toluene is 575 nm.

example 3

Production of 4-[1,5-diphenyl-2-pyrazolinyl-3)-N-(4-methoxyphenyl)]-naphta-limide

[0133] This compound is produced and cleaned as the product in example 1. The source products are 4-acetylnaphalic anhydride (21.6 g), benzaldehyde (9.54 g), n-anisidine (13 g), and phenylhydrazine (10.3 g).

[0134] The end product yield from 31.54 g of the corresponding unsaturated ketone is 31.6 g (83%).

[0135] The formed red crystals have a melting temperature of 268.degree. C.; they are soluble in common organic solvents and water-insoluble.

[0136] .sub.max lum. in toluene is 570 nm.

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Abstract

The invention pertains to a method for preparing derivatives of the pyrazolinylnaphthalic acid having the general formula where Ar1 and Ar2 are unsubstituted or substituted phenyl radicals bearing in the para position an alkylated or acylated oxy- or amino group, or a polynuclear aryl radical, and Ar3 is a substituted N-naphthalimid or 1,8-naphthylene-1',2'-benzimidazole. Compounds ofthe above general formula are high-efficient red organic luminophors and are used widely as luminescent components of dyes for plastics and liquid scintillators, in hydrogeology to study water streams, to label the chemical industry wastewaters, as laser dyes, etc.

Description

CROSS REFERENCE TO RELATED PATENT APPLICATIONS[0001] This application is related to and claims priority on Ukrainian patent application serial number 99127167, filed Dec. 28, 1999.[0002] The invention relates to a method for preparing derivatives of the pyrazolinylnaphthalic acid having the general formula 2[0003] where[0004] Ar.sub.1 and Ar.sub.2 are unsubstituted or substituted phenyl radicals bearing in the para position an alkylated or acylated oxy- or amino group, or a polynuclear aryl radical; and[0005] Ar.sub.3 is a substituted N-naphthalimid or 1,8-naphthylene-1',2'-b-enzimidazole.[0006] A method is known (see Ref. 1-USSR Author's Certificate No. 179,324, Cl. C09d) for preparing derivatives of pyrazolinylnaphthalic acid having the general formula 3[0007] where[0008] R.sub.1 is a unsubstituted or substituted aromatic or heterocyclic radical;[0009] R.sub.2 is a unsubstituted or substituted aromatic radical;[0010] R.sub.3 is an alkyl, aryl, alkoxy, or halogen.[0011] Compounds o...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C07D403/04C07D471/06C09B57/08C09B57/12
CPCC07D403/04C07D471/06C09B57/08C09B57/12
Inventor SHERSHUKOV, VICTOR M.SKRIPKINA, VALENTINA T.
Owner EMAGIN CORP
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