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The preparation method of 1-aryl-5-hydroxypyrazole

A technology of hydroxypyrazole and phenyl, which is applied in the field of preparation of 1-aryl-5-hydroxypyrazole, can solve the problem of low product yield and the like, and achieve the effects of wide source of raw materials, few reaction steps and easy operation.

Active Publication Date: 2016-08-31
湖南海利常德农药化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The object of the present invention is to provide a kind of hydrochloride that adopts arylhydrazine or arylhydrazine and methoxyacrylic acid Method for preparing 1-aryl-5-hydroxypyrazole by reaction of methyl ester in solvent

Method used

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  • The preparation method of 1-aryl-5-hydroxypyrazole
  • The preparation method of 1-aryl-5-hydroxypyrazole
  • The preparation method of 1-aryl-5-hydroxypyrazole

Examples

Experimental program
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Effect test

Embodiment 1

[0015] Add 17.9g (100mmol) p-chlorophenylhydrazine hydrochloride, 11.6g (100mmol) methyl methoxyacrylate, and 100mL methanol into the three-necked reaction flask. The temperature was raised to reflux for about 6 hours, and the reaction liquid was quantified by liquid chromatography, and the yield of 1-p-chlorophenyl-5-hydroxypyrazole was 81.3%.

Embodiment 2

[0017] Add 10.8 g (100 mmol) of phenylhydrazine, 11.6 g (100 mmol) of methyl methoxyacrylate, and 100 mL of methanol into the three-necked reaction flask. The temperature was raised to reflux for about 6 hours, and the reaction solution was quantified by liquid chromatography, and the yield of 1-phenyl-5-hydroxypyrazole was 85.7%.

Embodiment 3

[0019] Add 15.3g (100mmol) of 2-nitrophenylhydrazine, 11.6g (100mmol) of methyl methoxyacrylate, and 100mL of methanol into the three-necked reaction flask. The temperature was raised to 40° C. to react for about 6 hours, and the reaction liquid was quantified by liquid chromatography, and the yield of 1-p-nitrophenyl-5-hydroxypyrazole was 52.6%.

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Abstract

The invention discloses a preparation method for 1-aryl-5-hydroxy pyrazol. According to the preparation method, the 1-aryl-5-hydroxy pyrazol is prepared by reaction of aryl hydrazine or hydrochloride of the aryl hydrazine and methoxy methyl acrylate in a solvent, and the chemical reaction formula is as shown in the specification. The preparation method for 1-aryl-5-hydroxy pyrazol is simple, has few reaction steps, is easy to operate, has the product yield greater than 50%, which is much higher than that of the prior art, uses the raw materials of wide source, and is applicable to industrial production.

Description

technical field [0001] The present invention relates to a preparation method of 1-aryl-5-hydroxypyrazole. Specifically, it relates to a method for preparing 1-aryl-5-hydroxypyrazole by using arylhydrazine or hydrochloride of arylhydrazine and methyl methoxyacrylate as raw materials. Background technique [0002] 1-aryl-5-hydroxypyrazole and its derivatives have extensive and important uses, and are intermediates of various pesticides and pharmaceutical active compounds. Patent WO2010135536 discloses a class of 1-aryl-5-hydroxypyrazole The application of derivatives of 1-aryl-5-hydroxypyrazoles in reducing blood uric acid levels; patent US2004057588 discloses the application of a class of 1-aryl-5-hydroxypyrazole derivatives in the treatment of AIDS; patent WO2008023235 discloses a class of 1-aryl-5- Application of derivatives of -hydroxypyrazole in the treatment of thrombus. [0003] Regarding the synthesis of 1-aryl-5-hydroxypyrazole, there are probably the following synt...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D231/18
CPCC07D231/22
Inventor 胡志彬刘卫东杜升华黄超群兰世林熊莉莉伍音茵程超王艳丽
Owner 湖南海利常德农药化工有限公司