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Synthesis method of 2-amino-5-chlorobenzophenone

A technology of chlorobenzophenone and synthesis method, which is applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of expensive phenylboronic acid, harsh absolute anhydrous conditions, environmental pollution, etc., and achieve the reaction time Short, waste reduction, high yield effect

Inactive Publication Date: 2018-03-23
SHAANXI JUJIEHAN CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The synthetic method of 2-amino-5-chlorobenzophenone is as follows: it is generated by Friedel-Crafts acylation reaction of p-chloroaniline and benzoyl chloride, and the yield is 39%. This method needs an acylating reagent, and the reaction requires harsher Absolutely anhydrous conditions; phenylboronic acid and 2-amino-5-chlorobenzonitrile are generated by addition reaction as raw materials, and the yield is 96%, but the phenylboronic acid required for the reaction is more expensive; the more commonly used method is from phenylacetonitrile, The cyclization of p-chloronitrobenzene under the action of alkali produces 5-chloro-3-phenyl-2,1-benzoisoxazole, but the ferric chloride waste residue produced in the subsequent process has great pollution to the environment

Method used

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Examples

Experimental program
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Effect test

Embodiment 1

[0019] The synthetic method of 2-amino-5-chlorobenzophenone comprises the following steps:

[0020] (1) Mix ethanol, sodium hydroxide, p-chloronitrobenzene, and phenylacetonitrile with a mass concentration of 95%, first stir at 2000rpm for 30min, and then ultrasonically oscillate at 25°C for 1h. The conditions for ultrasonic oscillation are: Ultrasonic power 100W, frequency 40Hz; Among them, the mass ratio of ethanol, sodium hydroxide, p-chloronitrobenzene, and phenylacetonitrile with a mass concentration of 95% is 10:1.2:2:1.7;

[0021] (2) Microwave the product of step (1) under the condition of 200W power for 10min, add water to the system, filter, wash the filter residue with methanol for 3 times, and then dry it at 80°C for 5h to obtain 5- Chloro-3-phenyl-2,1-benzisoxazole;

[0022] (3) Mix tetrahydrofuran and triethylamine, then add 5-chloro 3-phenyl-2,1-benzisoxazole and palladium carbon catalyst to mix, pass nitrogen gas, replace air 8 times, and then pass hydrogen ga...

Embodiment 2

[0024] The synthetic method of 2-amino-5-chlorobenzophenone comprises the following steps:

[0025] (1) Mix ethanol, sodium hydroxide, p-chloronitrobenzene, and phenylacetonitrile with a mass concentration of 95%, first stir at 2000rpm for 30min, and then ultrasonically oscillate at 35°C for 1h. The conditions for ultrasonic oscillation are: Ultrasonic power 200W, frequency 40Hz; Among them, the mass ratio of ethanol, sodium hydroxide, p-chloronitrobenzene, and phenylacetonitrile with a mass concentration of 95% is 10:1.2:2:1.7;

[0026] (2) Heat the product of step (1) in a microwave for 10 minutes under the condition of a power of 400W, add water to the system, filter, wash the filter residue with methanol for 3 times, and then dry it at 80°C for 5 hours to obtain 5- Chloro-3-phenyl-2,1-benzisoxazole;

[0027] (3) Mix tetrahydrofuran and triethylamine, then add 5-chloro-3-phenyl-2,1-benzisoxazole and palladium-carbon catalyst to mix, pass in nitrogen, replace the air 10 tim...

Embodiment 3

[0029] The synthetic method of 2-amino-5-chlorobenzophenone comprises the following steps:

[0030] (1) Mix ethanol, sodium hydroxide, p-chloronitrobenzene, and phenylacetonitrile with a mass concentration of 95%, first stir at 2000rpm for 30min, and then ultrasonically oscillate at 30°C for 1h. The conditions for ultrasonic oscillation are: Ultrasonic power 200W, frequency 40Hz; Among them, the mass ratio of ethanol, sodium hydroxide, p-chloronitrobenzene, and phenylacetonitrile with a mass concentration of 95% is 10:1.2:2:1.7;

[0031] (2) Microwave the product of step (1) for 10 minutes under the condition of a power of 300W, add water to the system, filter, wash the filter residue with methanol for 3 times, and then dry it at 80°C for 5 hours to obtain 5- Chloro-3-phenyl-2,1-benzisoxazole;

[0032] (3) Mix tetrahydrofuran and triethylamine, then add 5-chloro 3-phenyl-2,1-benzisoxazole and palladium carbon catalyst to mix, pass nitrogen gas, replace air 9 times, and then p...

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PUM

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Abstract

The invention discloses a synthesis method of 2-amino-5-chlorobenzophenone, comprising the following steps: (1) mixing ethanol with a mass concentration of 95%, sodium hydroxide, p-chloronitrobenzene and phenylacetonitrile, Stir, then ultrasonically oscillate at 25-35°C; (2) microwave heating, add water to the system, filter, wash the filter residue with methanol, and then dry to obtain 5-chloro 3-phenyl-2,1 benzo Isoxazole; (3) Mix tetrahydrofuran and triethylamine, then add 5-chloro 3-phenyl-2,1 benzisoxazole and palladium carbon catalyst to mix, pass nitrogen, replace air, and then pass hydrogen To a pressure of 0.1MPa, magnetically stirred, then filtered, and the obtained filter residue was vacuum-dried to obtain 2-amino-5-chlorobenzophenone. The method provided by the invention has high product yield, which can reach 95%, short reaction time, reduced waste discharge, and the production method is environmentally friendly.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of 2-amino-5-chlorobenzophenone. Background technique [0002] 2-Amino-5-chlorobenzophenone derivatives are widely used in anti-cancer, anti-mitosis, β1 receptor antagonists, anti-osteoporosis, etc. It is an important intermediate of benzodiazepine hypnotic and sedative drugs, and also an important raw material for the synthesis of quinoline by Friedlander method. [0003] The synthetic method of 2-amino-5-chlorobenzophenone is as follows: it is generated by Friedel-Crafts acylation reaction of p-chloroaniline and benzoyl chloride, and the yield is 39%. This method needs an acylating reagent, and the reaction requires harsher Absolutely anhydrous conditions; phenylboronic acid and 2-amino-5-chlorobenzonitrile are generated by addition reaction as raw materials, and the yield is 96%, but the phenylboronic acid required for the reaction is ...

Claims

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Application Information

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IPC IPC(8): C07C221/00C07C225/22
CPCC07C221/00C07D261/20C07C225/22
Inventor 李长英
Owner SHAANXI JUJIEHAN CHEM CO LTD
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