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Method for preparing 4-chlorine-3-nitro methyl-phenoxide

A technology for nitroanisole and p-aminoanisole is applied in the field of synthesizing 4-chloro-3-nitroanisole, and can solve problems such as difficulty in industrialized production, high cost, and difficulty in popularizing chemical tests

Inactive Publication Date: 2005-05-25
YANGTZE RIVER PHARM GRP CO LTD +1
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Problems solved by technology

Document J.Prakt.Chem.N.F.127,128, pp20 has reported the laboratory synthetic method of 4-chloro-3-nitrophenetole, can synthesize 4-chloro-3-nitrophenethyl ether fully with this method, but Industrial production is difficult and expensive
Literature Tetrahedron Letters NO.2, pp151-154, 1978 and Aust.J.Chem., 1983, 36, pp1031 also report the synthesis of 4-chloro-3-nitroanisole, but chemical test is difficult to popularize, and simultaneously this The routes are all laboratory synthesis methods, and industrialization needs to solve a large number of technical problems

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  • Method for preparing 4-chlorine-3-nitro methyl-phenoxide

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Embodiment Construction

[0014] 1, the preparation of p-methoxyacetanilide (compound 2)

[0015] Add 13.1kg of acetic anhydride into a 20L reaction kettle, add 7.38kg of compound 1 (p-aminoanisole) under stirring, add 27.0g of p-aminoanisole and 32.4ml of water into a 250ml reaction bottle, and stir. Add 21.6ml of acetic anhydride, stir to form a solution, cool to room temperature, precipitate loose solids, filter a large amount of oil into the filtrate, wash with water to obtain a crude product, recrystallize with water, remove a small amount of oil with activated carbon, and obtain colorless flaky crystals The product was dried to obtain 20.5 g of p-methoxyacetanilide, yield: 56.6%, mp: 127°C.

[0016] 2, Preparation of 4-amino-3-nitroanisole (compound 4)

[0017] In a 50L reactor, add 7.8kg of p-methoxyacetanilide, 55g of sodium nitrate dissolved in 120ml of water, 180g of fuming nitric acid dissolved in 30kg of dichloromethane solution, after heating to reflux, stop heating, dropwise add 3.44kg o...

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Abstract

The invention discloses a method for industrially synthesizing 4-chloro-3-nitroanisole from p-aminoanisole, which uses p-aminoanisole as a raw material, undergoes aminoacetylation protection, nitration, amino deprotection, Chlorination synthesized 4-chloro-3-nitroanisole. The preparation method of the present invention can be represented by the following reaction formula: ∴ M in the molecular formula e For methyl.

Description

technical field [0001] The invention relates to a method for industrially synthesizing 4-chloro-3-nitroanisole from p-aminoanisole. Background technique [0002] 4-Chloro-3-nitroanisole as a natural product Vindorosine, Vindoline (TetrahedronLetters NO.2, pp 151-154, 1978) and COX-II inhibitor Iguratimod (T-614) (the drug is currently undergoing III Phase II clinical research, South Africa is conducting phase II clinical research, South Korea and China are conducting preclinical research) The main intermediates and starting materials synthesized have been industrialized abroad, and my country relies entirely on imports. Document J.Prakt.Chem.N.F.127,128, pp20 has reported the laboratory synthetic method of 4-chloro-3-nitrophenetole, can synthesize 4-chloro-3-nitrophenethyl ether fully with this method, but Industrial production is difficult and expensive. Literature Tetrahedron Letters NO.2, pp151-154, 1978 and Aust.J.Chem., 1983, 36, pp1031 also report the synthesis of 4-c...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C201/06C07C205/36C07C205/37
Inventor 李旭东王进义周春红张正艮杨方明薛春余
Owner YANGTZE RIVER PHARM GRP CO LTD
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