Green and efficient preparation method of rebamipide

A high-efficiency and green technology, applied in the field of green and high-efficiency preparation of rebamipide, can solve the problems of fewer synthesis steps, high raw material prices, and strong corrosion of equipment, and achieve the effect of simple route, easy industrial production, and low price

Active Publication Date: 2018-08-24
JINAN ASIA PHARMA TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are many kinds of raw materials used in this process, the reaction cycle is long, the energy consumption is large, and the equipment is highly corrosive
2. Using diethyl aminomalonate hydrochloride and p-chlorobenzoyl chloride as raw materials, catalyzed condensation with triethylamine to obtain diethyl 4-chlorobenzamidomalonate; finally, catalyzed hydrolysis and decarboxylation by potassium hydroxide Deribamipide; this method has fewer synthetic steps, but the price of raw materials is higher

Method used

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  • Green and efficient preparation method of rebamipide
  • Green and efficient preparation method of rebamipide
  • Green and efficient preparation method of rebamipide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] In a reaction flask, add 12g (0.1mol) of benzoic acid (0.1mol) and 20g (0.15mol) of diisopropylethylamine into 300mL of toluene, heat to 80-100°C, stir for 1 hour, then turn on the vacuum, and distill 100mL of toluene to obtain a solution A; 32g (0.3mol) of benzyl alcohol was added to 1000mL of toluene, heated to reflux, and 200mL of toluene was aliquoted to obtain a mixed solution B; solution A was placed at 10°C, and 27g (0.1 mol) of toluene solution 1000mL was slowly added dropwise to solution A, and after the dropwise addition was completed, it was slowly raised to 20°C, and the stirring reaction was continued for 3h. After TLC monitored that the reaction of the raw materials was complete, the reaction solution of solution A was washed three times with 500mL of saturated sodium bicarbonate solution. Filter to remove the solid produced during the washing process, and keep the filtrate A; heat the solution B to 85°C, and slowly add the filtrate A dropwise under the pro...

Embodiment 2

[0024] In a reaction flask, add 12g (0.1mol) of benzoic acid (0.1mol) and 8g (0.15mol) of ethylenediamine into 300mL of toluene, heat to 80-100°C, stir and react for 1 hour, then turn on the vacuum, and aliquot 100mL of toluene to obtain solution A; Add 32g (0.3mol) of benzyl alcohol into 1000mL of toluene, heat to reflux, divide 200mL of toluene aliquots, and obtain mixed solution B; put solution A at 10°C, dissolve 27g (0.1mol) of diphenylphosphoryl azide 1000mL of toluene solution was slowly added dropwise to solution A. After the dropwise addition, the temperature was raised slowly to 20°C, and the stirring reaction was continued for 3h. After the reaction of the raw materials was monitored by TLC, the reaction solution of solution A was washed three times with 500mL of saturated sodium bicarbonate solution, and filtered to remove Wash the solid produced during the washing process, and keep the filtrate A; heat the solution B to 85°C, and slowly add the filtrate A dropwise ...

Embodiment 3

[0026] In a reaction flask, add 12g (0.1mol) of benzoic acid (0.1mol) and 15g (0.15mol) of triethylamine into 300mL of toluene, heat to 80-100°C, stir and react for 1 hour, then turn on the vacuum, and aliquot 100mL of toluene to obtain solution A; Add 32g (0.3mol) of benzyl alcohol into 1000mL of toluene, heat to reflux, divide 200mL of toluene aliquots, and obtain mixed solution B; put solution A at 10°C, and dissolve 27g (0.1mol) of diphenylphosphoryl azide 1000mL of toluene solution was slowly added dropwise to solution A. After the dropwise addition, it was slowly raised to room temperature and continued to stir for 3 hours. After the reaction of the raw materials was monitored by TLC, the reaction solution of solution A was washed three times with 500mL of saturated sodium bicarbonate solution, and filtered to remove the washed solution. For the solid produced in the process, keep the filtrate A; heat the solution B to 85°C, and slowly add the filtrate A dropwise under th...

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Abstract

The invention belongs to the technical field of medical synthesis and in particular relates to a green and efficient preparation method of rebamipide. The synthesis method provided by the invention has a green and simple route and the price of raw materials is low, so that industrial production is easy to realize. The invention further discloses a novel method for preparing aniline from benzoic acid.

Description

technical field [0001] The invention belongs to the technical field of pharmaceutical synthesis, and in particular relates to a green and efficient preparation method of rebamipide. Background technique [0002] Rebamipide, trade name Membrano Star, chemical name 2-(4-chlorobenzamido)-3-(1,2-dihydro-2-oxo-4-quinolyl)propane Acid, is an anti-infective and anti-ulcer drug. The pharmacological mechanism of rebamipide is to enhance the defense ability of the gastric mucosa by increasing the synthesis of prostaglandins in the gastric mucosa, protect the gastric mucosa and accelerate the repair of the gastric mucosa. The activation of neutrophils and neutrophils has obvious inhibitory effect, and it also has obvious scavenging effect on oxygen free radicals. [0003] At present, there are mainly 2 kinds of processing routes for synthesizing rebamipide: 1. With 4-bromomethylquinolin-2-one and diethyl acetamidomalonate as raw materials, first condense under the catalysis of sodium...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/227
CPCC07D215/227
Inventor 彭立增孙彬王建华李冬梅
Owner JINAN ASIA PHARMA TECH
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