A kind of synthetic method of flunixin

A synthesis method and flunixin technology, applied in the field of chemical synthesis, can solve the problems of increasing production cost, low yield, low ethylene glycol efficiency, etc., and achieve the guarantee of product yield and quality, shorten reaction time, and reduce production. cost effect

Active Publication Date: 2020-07-14
济南久隆医药科技有限公司 +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method uses xylene as a high temperature or highly toxic solvent, and the reaction requirements are relatively high, while the yield is low, and post-processing is difficult in actual production.
2. According to US5484931, 2-chloronicotinic acid and 2-methyl-3-trifluoromethylaniline were used as raw materials, and p-toluenesulfonic acid was catalytically refluxed for more than 24 hours to obtain flunixin with a yield of 83%. The main raw materials in this method 2-Methyl-3-trifluoromethylaniline is used in excess, the reaction time is long, the post-treatment is complicated, the yield is not high, the overall production cost is high, and the economy is poor
3. Heterocycles, 38(10), 1994, 2243-2246 reported that 2-methyl-3-trifluoromethylaniline and 2-chloronicotinic acid ethyl ester were used as raw materials, ethylene glycol was used as solvent, and after 6 hours of reaction at 165°C The solvent is evaporated and hydrolyzed to obtain flunixin with a total yield of 77.4%. In this method, the reaction temperature is high, the efficiency of distilling off the high boiling point solvent ethylene glycol is low, the hydrolysis reaction and subsequent steps are complicated, the yield is low, and the economy is poor
The yield of this method is about 90%, which is suitable for industrial production, but the recovery of the solvent polyethylene glycol or ethylene glycol used in this method will relatively increase the production cost, and the treatment of copper-containing wastewater will also increase the cost of anhydrous treatment.

Method used

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  • A kind of synthetic method of flunixin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Add 300L water into a 1000L reactor, add 131.9kg (837.5mol) 2-chloronicotinic acid and 140kg 2-methyl-3-trifluoromethylaniline (800mol) respectively, stir, add 1.4kg perfluorosulfonic acid resin, and heat up After reacting for 2.5 hours at 65°C-70°C, filter with suction, adjust the pH of the filtrate to 4.5 with 60% sulfuric acid solution, stir for 15-20min, shake off the filter, wash the filter cake with 30kg of water, and dry the filter cake to obtain 230.1kg of flunixin , the yield is 97.1%, the purity is 99.9%, and the purity is detected according to the method in USP38, the same below.

Embodiment 2

[0036] Add 300L water into a 1000L reactor, add 131.9kg (837.5mol) 2-chloronicotinic acid and 140kg (800mol) 2-methyl-3-trifluoromethylaniline respectively, stir, add 1.4kg perfluorosulfonic acid resin, Raise the temperature to 70°C, react for 2.5 hours, then filter with suction, adjust the pH of the filtrate to 4.5 with 60% sulfuric acid solution, stir for 15-20 minutes, shake off the filter, wash the filter cake with 30 kg of water, and dry the filter cake to obtain 229.8 kg of flunixin. The yield is 97.0%, and the purity is 99.8%.

Embodiment 3

[0038] Add 300L water into a 1000L reactor, add 131.9kg (837.5mol) 2-chloronicotinic acid and 140kg (800mol) 2-methyl-3-trifluoromethylaniline respectively, stir, add 1.4kg recycled perfluorosulfonic acid resin , raised the temperature to 65°C, reacted for 2.5 hours, then filtered with suction, adjusted the pH of the filtrate to 4.5 with 60% sulfuric acid solution, stirred for 15-20 minutes, and filtered with a shaker, washed the filter cake with 30 kg of water, and dried the filter cake to obtain 229.6 kg of flunixin. Yield 96.9%, purity 99.9%.

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Abstract

The invention belongs to the technical field of chemical synthesis and particularly relates to a method for synthesizing flunixin. The method comprises that 2-chloronicotinic acid and 2-methyl-3-trifluoromethylaniline undergo a reaction under the catalysis of a perfluorosulfonic resin to produce flunixin. The perfluorosulfonic resin as a catalyst can react fast and realize a high yield of 97%.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a method for synthesizing flunixin. Background technique [0002] The chemical formula of flunixin: C 14 h 13 f 3 N 2 , the chemical name is 2-[[2-methyl-3-(trifluoromethyl)phenyl]amino]-3-pyridinecarboxylic acid, [0003] Structural formula: . [0004] Flunixin is the key raw material for preparing flunixin meglumine, and it is mainly prepared as flunixin meglumine for use. Flunixin meglumine (flunixin meglumine) is a new type of non-steroidal animal-specific antipyretic and analgesic drugs, which belongs to the niacin derivatives and is an inhibitor of cyclooxygenase. Developed by Schering-Plough in the 1990s (trade name: Banamine), it has been widely used in many countries such as the United States, France, Switzerland, Germany, and the United Kingdom. Flunixin meglumine has antipyretic, anti-inflammatory and analgesic effects. It can significan...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/80C07D213/803
CPCC07D213/80C07D213/803Y02P20/584
Inventor 殷习栋赵延东杨统鹏宋晶晶郑真真李志远
Owner 济南久隆医药科技有限公司
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