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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. The preparation method comprises the following steps: (1) mixing ethanol with the mass concentration of 95%, sodium hydroxide, parachloronitrobenzene and benzyl cyanide, mixing the mixture and performing ultrasonic oscillation on the mixture at the temperature of 25-35 DEG C for 1h; (2) performing microwave heating on aproduct obtained in step (1) for 10min, adding water in a system, filtering, washing filter residues with methanol three times and drying the filter residues, so as to obtain 5-chlorine-3-phenyl-2, 1-benzisoxazole; (3) mixing methanol, the 5-chlorine-3-phenyl-2, 1-benzisoxazole, a palladium carbon catalyst and ammonium formate, heating and refluxing for 2h, cooling to room temperature, filteringand performing vacuum drying on the filter residues. The method provided by the invention is high in product yield, short in reaction time and less in waste discharge and 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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