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A kind of synthetic method of 3-amino-5-(4-methoxyphenyl) pyrazole

The technology of a methoxyphenyl group and a synthesis method is applied in the synthesis field of 3-amino-5-pyrazole, can solve the problems of poor economic benefit and low yield in industrialized production, and achieves high market promotion value, high yield, The effect of improving the reaction yield

Active Publication Date: 2018-03-09
ITIC MEDCHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0014] The invention provides a synthetic method of 3-amino-5-(4-methoxyphenyl)pyrazole, which overcomes the low yield of 3-amino-5-(4-methoxyphenyl)pyrazole in the prior art, The problem of poor economic benefits of industrialized production

Method used

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  • A kind of synthetic method of 3-amino-5-(4-methoxyphenyl) pyrazole
  • A kind of synthetic method of 3-amino-5-(4-methoxyphenyl) pyrazole
  • A kind of synthetic method of 3-amino-5-(4-methoxyphenyl) pyrazole

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Embodiment 1

[0068] A kind of synthetic method of 3-amino-5-(4-methoxyphenyl) pyrazole, comprises the following operation steps:

[0069] The first step: Synthesis of 3-carbonyl-3-p-methoxyphenylpropionitrile:

[0070] Fully stir and mix 0.1mol methyl p-methoxybenzoate and 80mL isopropanol solution, add 0.2mol sodium hydride and 2g palladium catalyst, control the temperature at 80°C, add dropwise 0.2mol acetonitrile, and complete the dropwise addition within 1 hour;

[0071] After the dropwise addition was completed, the temperature was raised to 100°C and the reaction was stirred for 4 hours;

[0072] After the reaction was completed, the solution was filtered while it was hot, the filtered filtrate was naturally cooled to room temperature, and the precipitate was collected by suction filtration, and 20 mL of glacial acetic acid was added to the precipitate for washing and suction filtration, and recrystallized with acetone after suction filtration to obtain 3-carbonyl- 3-p-methoxyphenyl...

Embodiment 2

[0080] A kind of synthetic method of 3-amino-5-(4-methoxyphenyl) pyrazole, comprises the following operation steps:

[0081] The first step: Synthesis of 3-carbonyl-3-p-methoxyphenylpropionitrile:

[0082] Fully stir and mix 0.1mol methyl p-methoxybenzoate and 80mL isopropanol solution, add 0.2mol sodium hydride and 3g palladium catalyst, control the temperature at 90°C, add dropwise 0.2mol acetonitrile, and complete the dropwise addition within 1 hour;

[0083] After the dropwise addition was completed, the temperature was raised to 100°C and the reaction was stirred for 6 hours;

[0084] After the reaction was completed, the solution was filtered while it was hot, the filtered filtrate was naturally cooled to room temperature, and the precipitate was collected by suction filtration, and 20 mL of glacial acetic acid was added to the precipitate for washing and suction filtration, and recrystallized with acetone after suction filtration to obtain 3-carbonyl- 3-p-methoxyphenyl...

Embodiment 3

[0092] A kind of synthetic method of 3-amino-5-(4-methoxyphenyl) pyrazole, comprises the following operation steps:

[0093] The first step: Synthesis of 3-carbonyl-3-p-methoxyphenylpropionitrile:

[0094] Fully stir and mix 0.1mol methyl p-methoxybenzoate and 80mL isopropanol solution, add 0.2mol sodium hydride and 2g palladium catalyst, control the temperature at 85°C, add dropwise 0.2mol acetonitrile, and complete the dropwise addition within 1 hour;

[0095] After the dropwise addition was completed, the temperature was raised to 100°C and the reaction was stirred for 5 hours;

[0096] After the reaction was completed, the solution was filtered while it was hot, the filtered filtrate was naturally cooled to room temperature, and the precipitate was collected by suction filtration, and 20 mL of glacial acetic acid was added to the precipitate for washing and suction filtration, and recrystallized with acetone after suction filtration to obtain 3-carbonyl- 3-p-methoxyphenyl...

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Abstract

The invention discloses a synthesizing method of 3-amino-5-(4-methoxyphenyl) pyrazole. The synthesizing method is characterized in that p-methoxy methyl benzoate is used as raw material, 3-carbonyl-3-p-methoxyphenyl propionitrile is synthesized in the first step, and the 3-amino-5-(4-methoxyphenyl) pyrazole is synthesized in the second step. The synthesizing method has the advantages that palladium catalyst is added in the reaction process of the first step, reaction time can be shortened evidently, and reaction energy consumption can be lowered; tungsten-molybdenum-nickel catalyst is added in the reaction process of the second step, the mixed solution of ethyl ether and methanol is used to recrystallize reaction crude products, reaction yield and product purity can be increased effectively, and high economic benefits are achieved; the synthesizing method is simple in synthesizing process, short in time, high in yield, and high in economic benefit and market popularization value.

Description

Technical field: [0001] The invention relates to a synthesis method of 3-amino-5-(4-methoxyphenyl)pyrazole, which belongs to the field of chemical synthesis. Background technique: [0002] In recent years, heterocyclic compounds have attracted the attention of medical and pesticide researchers due to their remarkable physiological activities. In the process of contemporary drug research, because the 1, 3, 4, and 5- four positions of the pyrazole ring can undergo group changes, there are many types of pyrazole ring compounds, and the research on pyrazole compounds has become a new trend in recent years. One of the fastest growing fields in chemical R&D. [0003] There are many synthetic methods of pyrazole compounds, and the more common ones are: [0004] The hydrazine derivative is condensed with the 1,3 dicarbonyl compound, and the product is pyrazole or pyrazolone, and the position of the substituent in the compound is determined by the nature of the substituent. [000...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D231/38B01J29/80
CPCB01J29/48B01J29/7815B01J29/80B01J2229/18C07D231/38
Inventor 胡海威丁靓闫永平郑辉严辉
Owner ITIC MEDCHEM CO LTD