Chemical synthesis of 3,4,5-trioxyaniline

A technology of tribenzyloxyaniline and tribenzyloxybenzamide, which is applied in 3 fields, can solve the problems of low reduction efficiency and limitations, and achieve the effects of high reduction yield, low price and improved reaction yield

Inactive Publication Date: 2007-09-05
XIAMEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the reduction efficiency is low, and it is limited by conditions such as energy, electrolyzer and electrode materials.

Method used

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  • Chemical synthesis of 3,4,5-trioxyaniline
  • Chemical synthesis of 3,4,5-trioxyaniline

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Embodiment 1: 3,4,5-tribenzyloxymethyl benzoate: add methyl trihydroxybenzoate 1.84g (0.01mol), potassium carbonate 5.52g (0.04 mol), add 40 mL of solvent N, N-dimethylformamide in a nitrogen atmosphere, then slowly add 4 mL of benzyl bromide (0.034 mol) dropwise at an oil bath temperature of 55 ° C, stir it magnetically for 24 h, and pour it rapidly into cold water, filter to remove the solvent, and put the precipitate in a vacuum drying oven to dry overnight to obtain a light yellow crude product, which is finally reconstituted with a mixed solvent of ethyl acetate:petroleum ether (boiling range 60-90°C) with a volume ratio of 1:2 Crystallization of the crude product gave the target product as colorless crystals in a yield of 91%.

Embodiment 2

[0015] Example 2: Methyl 3,4,5-tribenzyloxybenzoate: except that acetone was used instead of N,N-dimethylformamide, other operating conditions were the same as in Example 1, and colorless crystals 3,4 were obtained. , 3.45 g of methyl 5-tribenzyloxybenzoate, the yield was 76%.

Embodiment 3

[0016] Example 3: 3,4,5-tribenzyloxybenzamide: add 1.39g (3mmol) of 3,4,5-tribenzyloxymethylbenzoate into a 250mL three-necked flask, and then add 200mL ethylene glycol solvent, the temperature gradually increased to 100°C with magnetic stirring, ammonia gas was introduced into it, the reaction time was 30h, and it was allowed to stand overnight, and a precipitate was precipitated, filtered and washed with water for 3 times to obtain a needle-like white solid, which was dried and weighed 1.12 g, the yield is 83.3%.

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Abstract

A process for chemically synthesizing 3,4,5-tribenzyloxy phenylamine includes such steps as reaction between 3,4,5-methyl trihydroxybenzoate and benzylbromin in inertial organic solvent, adding the resultant to ice water, filtering, depositing, baking, recrystallizing in the mixture of ethyl acetate and petroether to obtain 3,4,5-methyl tribenzyloxybenzoate, dissolving it in ethanediol solution, filling ammonia gas, cooling to educe out needle solid, filtering, washing to obtain 3,4,5-tribenzyloxy benzoylamine, dissolving it in methanol, adding sodium hypochlorite solution and sodium hydroxide, reaction to obtain 3,4,5-tribenzyloxy phenylamino formate, adding sodium hydroxide, hydrolysis, cooling, filtering washing and baking.

Description

technical field [0001] The present invention relates to a kind of synthetic method of 3,4,5-tribenzyloxyaniline, especially relate to a kind of with 3,4,5-trihydroxybenzoic acid methyl ester as starting raw material, through Williamson (Williamson) A method for synthesizing the target compound 3,4,5-tribenzyloxyaniline in three steps of synthesis, ammoniation, and Hofmann rearrangement. Background technique [0002] 3,4,5-Tribenzyloxyaniline is an important medicine and organic synthesis intermediate, which is widely used in the synthesis of anti-anginal drug Khellin. Literature (1. He Lifang, Guo Zhongzhong. The Present Situation and Prospect of Synthesis of Aromatic Amines. Yunnan Metallurgy, 2005, 34(3): 57-62; 2. Geissman T A. Halsall TG. Chromones. III. A Total Synthesis of Khellin. J .Am.Chem.Soc., 1951,73(3):1280-1284.) The reported method for preparing this type of aromatic amine compound is to obtain the nitro compound first, and then obtain the target product by r...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C217/90C07C213/02
Inventor 罗正鸿徐伟
Owner XIAMEN UNIV
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