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Synthesis method of ketoprofen

A synthesis method and technology of nitrile ethyl benzophenone, applied in the field of ketoprofen synthesis, can solve the problems of high hydrolysis cost of 3-nitrile ethyl benzophenone, difficult post-processing, long reaction time and the like, and achieve The effect of short reaction time, long time and mild reaction conditions

Active Publication Date: 2010-06-30
ZHEJIANG UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In order to solve the deficiencies in the prior art of high hydrolysis cost, long reaction time, difficult post-treatment and easy pollution of 3-nitrile ethyl benzophenone, the invention provides a method with reasonable process, high reaction yield and short reaction time , low production cost, clean and environmentally friendly ketoprofen synthetic method

Method used

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  • Synthesis method of ketoprofen
  • Synthesis method of ketoprofen

Examples

Experimental program
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Effect test

Embodiment 1

[0020] Dissolve 23.5g (0.1mol) of 3-nitrile ethyl benzophenone in 200ml of methanol, pour it into a three-necked flask, feed HCl gas, and react at room temperature for 1.5 hours. TLC will track the reaction. When the raw material point disappears, the reaction ends 8g (0.2mol) NaOH and 100ml water were added to the solution, and the mixture was refluxed at 70°C for 2 hours. The reaction liquid was cooled to room temperature, and the pH value was adjusted to 3.5 with 1 mol / L hydrochloric acid, and a solid was precipitated. Filtrate through filter paper, put the filter cake into an oven to dry, recrystallize the crude product with methanol (300 mL), filter through filter paper, put the filter cake into an oven to dry, and obtain 22.8 g of ketoprofen pure product, which is a white crystal with a melting point of 95 to 96° C. Rate 90%.

Embodiment 2

[0022] Dissolve 23.5g (0.1mol) of 3-nitrile ethyl benzophenone in 100ml of methanol, pour it into a three-necked flask, feed HCl gas, react at room temperature for 2 hours, and add 12g (0.3mol l) NaOH and 100ml of water were refluxed at 70°C for 2 hours. The reaction solution was cooled to room temperature, and the pH value was adjusted to about 3.5 with hydrochloric acid, and a solid was precipitated. Filter through filter paper, dry, recrystallize the filter cake with methanol (300 mL), filter through filter paper, put the filter cake into an oven and dry to obtain 23.6 g of pure ketoprofen, which is a white crystal with a melting point of 95 to 96° C. and a yield of 93%.

Embodiment 3

[0024] Dissolve 23.5g (0.1mol) of 3-nitrile ethyl benzophenone in 100ml of methanol, pour it into a three-necked flask, feed HCl gas, react at room temperature for 1.5 hours, and add 11.2g (0.2mol )KOH and 50ml of water, reflux at 70°C for 2 hours. The reaction solution was cooled to room temperature, and the pH value was adjusted to about 3.5 with hydrochloric acid, and a solid was precipitated. Filter, dry, recrystallize the filter cake with methanol (300 mL), filter, put the filter cake into an oven to dry, and obtain 24.1 g of pure ketoprofen as white crystals, melting point 95-96° C., yield 95%.

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Abstract

The invention relates to a synthesis method of ketoprofen shown as a formula (I), which comprises the following steps: making 3-nitrile ethyl benzophenone shown as a formula (II) to react with a sufficient amount of chlorine hydride gas in an alcohols reaction solvent for producing intermediate compounds shown as a formula (III); adding 0.1 to 10 mol / L inorganic base water solution for hydrolysisreaction after the reaction completion; adding acid for regulating the pH value to 3 to 4 after the hydrolysis completion; and carrying out separation treatment on reaction liquid to obtain the ketoprofen shown as the formula (I). The invention has the advantages of high reaction yield, low cost, mild reaction conditions, no condensation by-product, low energy consumption and simple and convenient operation, and is suitable for industrial production.

Description

(1) Technical field [0001] The invention relates to a method for synthesizing ketoprofen, in particular to the method of firstly activating the nitrile group and then hydrolyzing to synthesize ketoprofen. (2) Background technology [0002] Ketoprofen, whose chemical name is 3-benzoyl-α-methylphenylacetic acid, is a non-steroidal anti-inflammatory analgesic with anti-inflammatory, antipyretic and analgesic effects. The analgesic effect is superior to similar drugs and lasts for a long time, with less toxic and side effects, and good safety and tolerance. It was first listed in France in 1973, and officially entered China in the 1980s. Now it has developed various dosage forms such as oral tablets, patches, and diaphragms, and has been widely used at home and abroad. [0003] Before the present invention was made, most of the chemical synthesis methods of prior art ketoprofen obtained ketoprofen through the hydrolysis of key intermediate 3-nitrile ethyl benzophenone, and hydr...

Claims

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Application Information

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IPC IPC(8): C07C59/84C07C51/08
Inventor 金灿苏为科胡范车大庆王其亮
Owner ZHEJIANG UNIV OF TECH
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