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Method for catalytically oxidizing quinclorac

A kind of quinclorac, catalytic oxidation technology, applied in the direction of organic chemistry and the like, can solve the problems of long oxidation time, poor product quality, low yield and the like, and achieve the effects of short oxidation time, low cost and high yield

Inactive Publication Date: 2012-11-28
江苏绿利来股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of this invention is to provide a method for catalytic oxidation synthesis of quinclorac, to overcome the shortcomings of low yield, poor product quality, long oxidation time, etc.

Method used

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  • Method for catalytically oxidizing quinclorac
  • Method for catalytically oxidizing quinclorac
  • Method for catalytically oxidizing quinclorac

Examples

Experimental program
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Embodiment 1

[0030] First add 125mL of water to the reaction bottle A, and add 560g of concentrated sulfuric acid (98%) dropwise under stirring. After the dropwise addition, start to add 250g of 3-chloro-2-methylaniline, 2g of potassium iodide, and start to add 185g of glycerol dropwise. Generally, the dropwise addition ends in 3 hours, and the dropping temperature is kept at 148-150°C. Keep warm for 2.5 hours, add 400mL of water at the end of the heat preservation, cool down to below 40°C, add 1000ml of petroleum ether (boiling range of 60-90°C). Start adding dilute lye (32%) dropwise. When the pH reaches 9-10, stop the dropwise addition, and separate the layers after standing for half an hour. The upper material is filtered, the filter cake is washed with 200ml of petroleum ether, the filtrates are combined, and distilled at atmospheric pressure until no fraction comes out. After the distillation was finished, 1000 ml of o-dichlorobenzene was added for use in the next step of chlorinati...

Embodiment 2

[0034] First add 125mL of water to the reaction bottle A, and add 560g of concentrated sulfuric acid (98%) dropwise under stirring. After the dropwise addition, start to add 250g of 3-chloro-2-methylaniline, 2g of potassium iodide, and start to add 185g of glycerol dropwise. Generally, the dropwise addition ends in 3 hours, and the dropping temperature is kept at 148-150°C. Keep warm for 2.5 hours, add 400mL of water at the end of the heat preservation, cool down to below 40°C, add 1000ml of petroleum ether (boiling range of 60-90°C). Start adding dilute lye (32%) dropwise. When the pH reaches 9-10, stop the dropwise addition, and separate the layers after standing for half an hour. The upper material is filtered, the filter cake is washed with 200ml of petroleum ether, the filtrates are combined, and distilled at atmospheric pressure until no fraction comes out. After the distillation was finished, 1000 ml of o-dichlorobenzene was added for use in the next step of chlorinati...

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Abstract

The invention discloses a method for catalytically oxidizing quinclorac, which takes m-chloro-o-toluidine and glycerol as raw materials to carry out cyclization reaction for preparing 7-chlorine-8-methyl-quinolin, chlorination is carried out through the 7-chlorine-8-methyl-quinolin and chlorine gas, so 3, 7-dichloro-8-(chloromethyl) quinoline is obtained, finally, concentrated nitric acid, sulfuric acid and an oxidation catalyst are used to oxidize the 3, 7-dichloro-8-(chloromethyl) quinoline, wherein the oxidation catalyst is alkyl sulfonic acid, alkyl sulfuric acid or alkyl benzene sulfonic acid. The synthetic method uses the oxidation catalyst, so the reaction yield is greatly increased, the total yield can reach above 70%, and the quinclorac with higher content is obtained; and the method has the characteristics of simplicity in operation, high yield, short oxidization time, low cost and the like.

Description

technical field [0001] The invention belongs to the field of pharmaceutical compounds, in particular to a catalytic oxidation synthesis method of quinclorac. Background technique [0002] The chemical name of quinclorac (Quinclorac) is 3,7-dichloro-8-quinolinecarboxylic acid, and its structural formula is [0003] [0004] According to the report of DE3108873, using m-chloro-o-toluidine and glycerol as raw materials, the intermediate 7-chloro-8-methylquinoline was first prepared, and then chlorine gas was passed through dichlorobenzene to generate 3,7-dichloro-8-chloro Methyl quinoline, and then oxidized with concentrated nitric acid in concentrated sulfuric acid to obtain the target compound. The yield of this process is low, the total yield is only about 58%, and the content of quinclorac is low, generally only 78% to 86%. To obtain a high content of quinclorac of about 98%, it is usually obtained by washing with a solvent for many times. The main reason is that the ...

Claims

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Application Information

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IPC IPC(8): C07D215/48
Inventor 许网保魏明阳臧伟新虞国新
Owner 江苏绿利来股份有限公司
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