Preparation method of 2-amino-5- chlorobenzophenone

A technology of chlorobenzophenone and amino, which is applied in the field of preparation of 2-amino-5-chlorobenzophenone, can solve the problems of harsh absolute anhydrous conditions, environmental pollution, expensive phenylboronic acid, etc., and achieve short reaction time , high yield, and environmentally friendly production methods

Inactive Publication Date: 2018-02-16
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
Comparison scheme
Effect test

Embodiment 1

[0019] A preparation method of 2-amino-5-chlorobenzophenone, comprising the following steps:

[0020] (1) According to the mass ratio of 10:1.2:2:1.7, mix ethanol, sodium hydroxide, p-chloronitrobenzene, and phenylacetonitrile with a mass concentration of 95%, first stir at 2000rpm for 30min, and then stir at 25% Under the conditions of ultrasonic power 100W and frequency 40Hz, ultrasonic oscillation for 1h;

[0021] (2) Microwave the product of step (1) for 10 minutes at a power of 200W, add water to the system, filter, wash the filter residue 3 times with methanol, and then dry to obtain 5-chloro-3-phenyl-2, 1 benzisoxazole;

[0022] (3) According to the mass ratio of 30:2:0.08:1.7, methanol, 5-chloro-3-phenyl-2,1-benzisoxazole, palladium-carbon catalyst, and ammonium formate were mixed, and heated to reflux at 50°C for 2 hours, Naturally cool to room temperature, then filter, and vacuum-dry the resulting filter residue at 50° C. for 4 hours to obtain 2-amino-5-chlorobenzo...

Embodiment 2

[0024] A preparation method of 2-amino-5-chlorobenzophenone, comprising the following steps:

[0025] (1) According to the mass ratio of 10:1.2:2:1.7, mix ethanol, sodium hydroxide, p-chloronitrobenzene, and phenylacetonitrile with a mass concentration of 95%, first stir at 2000rpm for 30min, and then stir at 35% Under the conditions of ultrasonic power 200W and frequency 40Hz, ultrasonic oscillation for 1h;

[0026] (2) Microwave the product of step (1) for 10 minutes at a power of 400W, add water to the system, filter, wash the filter residue 3 times with methanol, and then dry to obtain 5-chloro-3-phenyl-2, 1 benzisoxazole;

[0027] (3) According to the mass ratio of 30:2:0.08:1.7, mix methanol, 5-chloro-3-phenyl-2,1-benzisoxazole, palladium-carbon catalyst, and ammonium formate, and heat and reflux at 60°C for 2 hours. Naturally cool to room temperature, then filter, and vacuum-dry the resulting filter residue at 50° C. for 4 hours to obtain 2-amino-5-chlorobenzophenone....

Embodiment 3

[0029] A preparation method of 2-amino-5-chlorobenzophenone, comprising the following steps:

[0030] (1) According to the mass ratio of 10:1.2:2:1.7, mix ethanol, sodium hydroxide, p-chloronitrobenzene, and phenylacetonitrile with a mass concentration of 95%, first stir at 2000rpm for 30min, and then stir at 30 Under the conditions of ultrasonic power 100W and frequency 40Hz, ultrasonic oscillation for 1h;

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

[0032] (3) According to the mass ratio of 30:2:0.08:1.7, methanol, 5-chloro-3-phenyl-2,1-benzisoxazole, palladium-carbon catalyst, and ammonium formate were mixed, and heated to reflux at 53°C for 2 hours, Naturally cool to room temperature, then filter, and vacuum-dry the resulting filter residue at 50° C. for 4 hours to obtain 2-amino-5-chloroben...

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Abstract

The invention discloses a preparation 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 for 1 h; (2) Microwave the product of step (1) for 10 min, add water to the system, filter, wash the filter residue 3 times with methanol, and then dry to obtain 5‑ Chlorine 3-phenyl-2,1-benzisoxazole; (3) Mix methanol, 5-chloro-3-phenyl-2,1-benzisoxazole, palladium-carbon catalyst, ammonium formate, heat and reflux for 2h, Cool to room temperature, filter, and vacuum-dry the filter residue. The method provided by the invention has high product yield, 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 preparation 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 i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C225/22C07C221/00C07D261/20
CPCC07C221/00C07D261/20C07C225/22
Inventor 李长英
Owner SHAANXI JUJIEHAN CHEM CO LTD
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