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Preparation method of 3-methyl-4-aminobenzoic acid

A technology of aminobenzoic acid and nitrobenzoic acid, which is applied to the preparation of organic compounds, chemical instruments and methods, and cyanide reaction preparation, can solve the problems of complex operation, many by-products, and high cost, and achieve simple operation and improved The effect of product yield and product cost reduction

Inactive Publication Date: 2017-06-13
中涛新材料有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] The purpose of the present invention is to provide a kind of 3-methyl-4-aminobenzoic acid in order to solve the technical problems of low yield, many by-products, complicated operation and high cost in the preparation method of existing 3-methyl-4-aminobenzoic acid. -Method for the preparation of aminobenzoic acid

Method used

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  • Preparation method of 3-methyl-4-aminobenzoic acid
  • Preparation method of 3-methyl-4-aminobenzoic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] In the reaction flask equipped with reflux condenser, thermometer and stirrer, add 36.0 grams (0.2mol) of 3-methyl-4-nitrobenzoic acid, 0.3 grams (0.0009mol) of tetrabutylammonium bromide, and 300 Mix 1 ml of water evenly, then add 16.8 g (0.3 mol) of reduced iron powder, 3.0 g (0.056 mol) of ammonium chloride, 2 ml of concentrated hydrochloric acid, heat to 85°C under stirring, and react under reflux for 6 hours until the raw material 3- The reaction of methyl-4-nitrobenzoic acid is complete;

[0037] Cool down to 5°C, add sodium carbonate and activated carbon for decolorization for 0.5 hours, the addition of sodium carbonate and activated carbon is respectively 1.5% of the mass of 3-methyl-4-nitrobenzoic acid, adjust the pH value to be alkaline, filter the iron sludge, Wash twice with 5% sodium carbonate solution, mix and filter the mother liquor and cleaning solution to obtain a light yellow solution;

[0038] Add sulfuric acid to the above light yellow solution, ad...

Embodiment 2

[0042]In the reaction flask equipped with reflux condenser, thermometer and stirrer, add 36.0 grams (0.2mol) of 3-methyl-4-nitrobenzoic acid, 0.9 grams (0.0028mol) of tetrabutylammonium bromide and 300 milliliters Stir the water evenly, then add 16.8 g (0.3 mol) of reduced iron powder, 3.0 g (0.056 mol) of ammonium chloride, and 2 ml of concentrated hydrochloric acid, heat to 110°C under stirring, and react under reflux for 2 hours until the raw material 3-formazol Base-4-nitrobenzoic acid reacts completely;

[0043] Cool down to 35°C, add sodium carbonate and activated carbon for decolorization for 0.5 hour, the amount of sodium carbonate and activated carbon added is 1.5% of the mass of 3-methyl-4-nitrobenzoic acid respectively, and the pH value is adjusted to be alkaline. Filter the iron sludge, wash twice with 5% sodium carbonate solution, mix and filter the mother liquor and cleaning solution to obtain a light yellow solution;

[0044] Add sulfuric acid to the above ligh...

Embodiment 3

[0047] In the reaction flask equipped with reflux condenser, thermometer and stirrer, add 36.0 grams (0.2mol) of 3-methyl-4-nitrobenzoic acid, 0.3 grams (0.0009mol) of tetrabutylammonium bromide, and 150 Mix 1 ml of water evenly, then add 16.8 g (0.3 mol) of iron powder, 3.0 g (0.056 mol) of ammonium chloride, and 1 ml of concentrated hydrochloric acid, heat to 95°C under stirring, and react under reflux for 2.5 hours until the raw material 3-formazol Base-4-nitrobenzoic acid reacts completely;

[0048] Cool down to 10°C, add sodium carbonate and activated carbon for decolorization for 0.5 hour, the addition of sodium carbonate and activated carbon is respectively 1.5% of the mass of 3-methyl-4-nitrobenzoic acid, adjust the pH value to be alkaline, filter the iron sludge, Wash twice with 5% sodium carbonate solution, mix and filter the mother liquor and cleaning solution to obtain a light yellow solution.

[0049] Add sulfuric acid to the above light yellow solution, adjust t...

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Abstract

The invention provides a preparation method of 3-methyl-4-aminobenzoic acid and belongs to the technical field of chemical synthesis. According to the method, 3-methyl-4-nitrobenzoic acid and a quaternary ammonium salt type phase-transfer catalyst are added to a reaction device, a solvent is added, the mixture is stirred uniformly, reduced iron powder and protonic acid are added to react, and a reaction liquid is obtained; then the reaction device is cooled, sodium carbonate and activated carbon are added for decoloration, the PH value is adjusted to be alkaline, iron mud is filtered and washed twice with a sodium carbonate solution, a filtered stock and cleaning fluids are mixed, and a light yellow solution is obtained; acid is added to the light yellow solution until the PH value is adjusted to be slightly acid, off white precipitates are separated out, filtered, washed with water and dried, and 3-methyl-4-aminobenzoic acid is obtained. The preparation method is simple, low in cost and more suitable for industrial production, and the product yield reaches 90.1% at most.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, in particular to a method for preparing 3-methyl-4-aminobenzoic acid. [0002] technical background [0003] 3-Methyl-4-aminobenzoic acid is an important intermediate in the synthesis of dyes and medicines, and is mainly used in the synthesis of Telmisartan in the pharmaceutical industry. Telmisartan is an angiotensin (AT) Ⅱ receptor antagonist with the longest half-life, and is the antihypertensive drug with the longest antihypertensive effect of sartan. Due to the long-term dependence of hypertensive patients on drugs, this product is the only drug among angiotensin Ⅱ receptor antagonists that only needs to be taken once a day, and the incidence of side effects is significantly lower than that of similar drugs. At the same time, with the aging trend of the global population, there is a greater need for effective and safe antihypertensive drugs AT II antagonists. Telmisartan is the lo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C227/04C07C229/60
CPCC07C227/04C07C229/60
Inventor 田蕾王佳旭孙豪健刘晓黎蔡雨轩孙倩
Owner 中涛新材料有限公司
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