Preparation process of ketoprofen

A preparation process and ketoprofen technology, applied in the field of medicine, can solve the problems of expensive raw materials, long reaction route, low total yield and the like, and achieve the effects of avoiding Grignard reaction, low equipment requirements and easy operation.

Active Publication Date: 2017-05-31
IANGSU COLLEGE OF ENG & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Compared with the above two processes, this process route has been greatly improved, but the raw materials used in this process are more expensive, the reaction route is longer, and the total yield is lower

Method used

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  • Preparation process of ketoprofen
  • Preparation process of ketoprofen
  • Preparation process of ketoprofen

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] Example 1. Preparation of 4-acetamidobenzophenone (1).

[0064] 140 g of benzoyl chloride and 148 g of acetanilide were dissolved in 400 g of chloroform, 145 g of aluminum trichloride was added, and reacted at room temperature for 8 hours. After the reaction, the reaction solution was slowly poured into 500 ml of dilute hydrochloric acid ice water, and vigorously stirred while pouring. The liquid was separated, the organic layer was dried over anhydrous sodium sulfate, the solvent was recovered under reduced pressure, and petroleum ether: ethyl acetate = 1:1 was recrystallized to obtain 222 g of intermediate 4-acetamidobenzophenone (1), with a yield of 93%.

Embodiment 2

[0065] Example 2. Preparation of 2-acetylamino-5-benzoyl-acetophenone (2)

[0066] Dissolve 120g of 4-acetamidobenzophenone, 67g of aluminum trichloride in 400g of ethyl acetate, slowly add 40g of acetyl chloride dropwise under ice bath, and finish dropping in 30 minutes. The reaction solution was slowly poured into 150 ml of dilute hydrochloric acid in ice water, stirred while pouring, and separated, the organic layer was dried over anhydrous sodium sulfate, and the solvent was recovered under reduced pressure. Petroleum ether: ethyl acetate = 5:3 recrystallized to obtain 2- Acetylamino-5-benzoyl-acetophenone (2) 139 g, yield 94%.

Embodiment 3

[0067] Example 3. Preparation of 2-acetyl-4-benzoylaniline (3)

[0068] 139g of 2-acetamido-5-benzoyl-acetophenone, dissolved in 200ml of ethanol, added 100ml of 40% dilute hydrochloric acid, heated to reflux for 2h, after the reaction was completed, cooled to room temperature, and added dropwise sodium carbonate solution to alkaline. Extracted with ethyl acetate, dried over anhydrous sodium sulfate, recovered the solvent under reduced pressure, and recrystallized petroleum ether: ethyl acetate = 1:1 to obtain 109.6 g of 2-acetyl-4-benzoylaniline (3), with a yield of 98% .

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Abstract

The invention discloses a preparation process of ketoprofen. A method takes benzoyl chloride and acetanilide as starting raw materials, and the ketoprofen is prepared through the steps of acylating, carting out acylation, de-protecting, hydrolyzing, carrying out diazotization reduction, carrying out Darzens reaction, oxidizing and the like. According to the method disclosed by the invention, the raw materials have cheap prices and are easy to obtain; the process is easy to realize and a hazardous process does not exist in the reaction; the yield is high and reaction conditions are moderate; the preparation method is simple and convenient to operate and has low requirements on equipment.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to a preparation process of ketoprofen. Background technique [0002] Ketoprofen (Ketoprofen, KP) is also known as ketoprofen, ketoprofen, Youbufen, Youprofen or Profenid, and its chemical name is α-methyl-3-benzoylphenylacetic acid [2- (3-Benzoylphenyl)propanoic acid[CAS:22071-15-4]] is an excellent 2-aryl propanoic acid non-steroid developed by Farge, Messer and Moutounier, chemists from the French Rhone-Poulenc company in 1967 Anti-inflammatory analgesic drugs. Its mechanism of action is mainly through inhibiting the biological activity of cyclooxygenases (COXs) and lipoxygenases (LOXs) in the body, thereby inhibiting the synthesis of prostaglandins (PGs) and leukotrienes (LTs), which are prostaglandins (LTs), and have anti-brady-shock effects. Peptides release, scavenge hydroxyl radicals, and stabilize lysosomal membrane activity, thereby producing good antipyreti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/285C07C59/84
CPCC07C45/65C07C51/285C07C221/00C07C231/12C07C59/84C07C49/784C07C225/22C07C233/33
Inventor 冯成亮尹桂波严宾
Owner IANGSU COLLEGE OF ENG & TECH
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