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Synthesis method of mefenamic acid

A technology of mefenamic acid and its synthesis method, which is applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of low production cost, dark product color, low product yield, etc., and achieve improved yield , reduce the amount of tar produced, reduce the effect of side reactions

Active Publication Date: 2016-09-21
JIANGSU BEIHEDE CHEM +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] The invention provides a method for synthesizing mefenamic acid, which has the advantages of high reaction yield, high product quality and low production cost, and solves the problems of low product yield and dark product color existing in the existing preparation method question

Method used

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  • Synthesis method of mefenamic acid
  • Synthesis method of mefenamic acid

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Embodiment 1

[0029] The preparation of embodiment 1 mefenamic acid

[0030] Put 10g of DMF into a 250mL four-neck flask, raise the temperature to 80°C, put in 27g of o-chlorobenzoic acid, until the o-chlorobenzoic acid is completely dissolved, add 25g of sodium carbonate to form a salt, and keep at 80°C for half an hour. Connect the water separator, add 25g of toluene to separate the water until no water comes out. Afterwards, 0.5 g of manganese acetate catalyst and 22.5 g of 2,3-dimethylaniline were added, and the temperature was kept at 120-130°C. Sampling HPLC central control, when o-chlorobenzoic acid <1%, add 100mL water, add dilute sulfuric acid to adjust the pH to 2, filter with suction, and dry to obtain about 39.5g off-white solid with a molar yield of 94.8%. The nuclear magnetic detection data and The reaction formulas are as follows.

[0031] 1 H NMR(DMSO):δ2.10(s,3H,-CH 3 ),2.28(s,3H,-CH 3 ),6.68~7.90(m,7H,Ar-H),9.46(s,-NH).

[0032]

Embodiment 2

[0033] The preparation of embodiment 2 mefenamic acid

[0034] Put 10g of DMF into a 250mL four-neck flask, raise the temperature to 80°C, put in 27g of o-chlorobenzoic acid, until the o-chlorobenzoic acid is completely dissolved, add 25g of sodium carbonate to form a salt, and keep at 80°C for half an hour. Connect the water separator, add 25g of toluene to separate the water until no water comes out. Afterwards, 0.5 g of catalyst manganese sulfate and 22.5 g of 2,3-dimethylaniline were added, and the temperature was kept at 120-130°C. Sampling is controlled by HPLC. When o-chlorobenzoic acid is <1%, add 100mL of water, add dilute sulfuric acid to adjust the pH to 2, filter with suction, and dry to obtain about 38.7g of off-white solid with a molar yield of 93.0%. The NMR detection data is as follows :

[0035] 1 H NMR(DMSO):δ2.10(s,3H,-CH 3 ),2.28(s,3H,-CH 3 ), 6.68~7.90 (m, 7H, Ar-H), 9.46 (s, -NH).

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Abstract

The invention discloses a synthesis method of mefenamic acid. The method comprises the following steps: by using o-chloro-benzoic acid as a raw material, salifying by using a non-proton polar solvent in the presence of an acid-binding agent to obtain o-chloro-benzoate; and under the action of a dehydrating agent, carrying out condensation reaction on the o-chloro-benzoate and 2,3-dimethylaniline by using metal manganese powder or manganese salt as a catalyst, and acidifying to obtain the mefenamic acid. The synthesis method disclosed by the invention has the advantages of high reaction yield, high product quality and low production cost, and solves the problems of lower product yield and deep product color in the existing preparation method.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a method for synthesizing mefenamic acid. Background technique [0002] Mefenamic acid, also known as mefenamic acid, paracetamol, etc., its English name is Mefenamic Acid, its chemical name is N-2,3-xylylanthranilic acid, and its structural formula is shown in the following formula. [0003] [0004] Mefenamic acid is a non-steroidal anti-inflammatory drug. Its main function is to stabilize the protein structure of the cell membrane and interfere with tissue metabolism by inhibiting the synthesis of prostaglandins and proteolytic enzymes. [0005] Compared with the same type of non-steroidal anti-inflammatory drugs, the anti-inflammatory effect of mefenamic acid is obviously stronger than that of flufenamic acid and clofenamic acid, so it is more widely used. Clinically, it is mainly used for the treatment of rheumatism, rheumatoid arthritis, dysmenorrhea, headache...

Claims

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Application Information

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IPC IPC(8): C07C229/58C07C227/08
CPCC07C227/08C07C229/58
Inventor 吴文良卢小逸张启明王诚
Owner JIANGSU BEIHEDE CHEM
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