Synthesis method of mesalazine drug intermediate 5-aminosalicylic acid

A technology of aminosalicylic acid and mesalazine, which is applied in the preparation of pharmaceutical intermediates and the synthesis of 5-aminosalicylic acid, a mesalazine pharmaceutical intermediate, can solve complex synthesis methods, many intermediate links in the reaction, and short reaction time. More than 16 hours, etc., to achieve the effect of increasing the reaction yield, increasing the reaction yield, and shortening the reaction time

Active Publication Date: 2016-10-12
海宁经开产业园区开发建设有限公司
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Problems solved by technology

[0003] He Xin (He Xin, Liu Xiujie, Si Hongqiang, Ma Bojun. Synthesis of 5-aminosalicylic acid [J]. Journal of Tianjin University of Technology, 2009, 03:64-66.) using salicylic acid as raw material, respectively Concentrated nitric acid and dilute nitric acid are used as nitrating reagents, and the reaction solution after nitration is recrystallized with water to synthesize 5-aminosalicylic acid, but this synthetic method is too complicated, there are many intermediate links in the reaction, the reaction time exceeds 16 hours, and the reaction yield is less than 25%. %, therefore, it is necessary to propose a new synthetic method

Method used

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Embodiment 1

[0023] A kind of synthetic method of mesalazine medicine intermediate 5-aminosalicylic acid, comprises the steps:

[0024] A. In the reaction vessel equipped with a stirrer and a reflux condenser, add 0.78mol of azobenzene salicylate, 230ml of sodium sulfite solution with a mass fraction of 25%, and 2-hydroxyl-5-methyl- 170ml of 3-nitropyridine solution, control the stirring speed at 160rpm, slowly add 0.83mol of molybdenum chloride powder, control the addition time at 3h, raise the solution temperature to 80°C, and react for 7.5h;

[0025] B, adding mass fraction is 210ml of xylene solution of 19%, lowers solution temperature to 16 ℃, separates out solid, is recrystallized in the cyclohexanone solution of 48% in 600ml mass fraction, obtains needle crystal, with 560ml mass fraction Dissolve 24% oxalic acid solution, decolorize with molecular sieve, filter, add 200ml of N-methylformamide solution with a mass fraction of 69% to the filtrate, reduce the temperature of the solutio...

Embodiment 2

[0027] A kind of synthetic method of mesalazine medicine intermediate 5-aminosalicylic acid, comprises the steps:

[0028] A, in the reaction vessel that agitator, reflux condenser are installed, add azobenzene salicylic acid 0.78mol, mass fraction is 25% sodium sulfite solution 220ml, mass fraction is 36% 2-hydroxyl-5-methyl- 150ml of 3-nitropyridine solution, control the stirring speed at 130rpm, slowly add 0.83mol of molybdenum chloride powder, control the addition time at 2h, increase the solution temperature to 79°C, and react for 7h;

[0029] B. Add 190ml of xylene solution with a mass fraction of 19%, lower the temperature of the solution to 13°C, precipitate a solid, and recrystallize in a 48% cyclohexanone solution with a mass fraction of 600ml to obtain needle-like crystals, which are dissolved in 530ml of oxalic acid solution , molecular sieve decolorization, filtering, adding 200ml mass fraction to the filtrate is 68% N-methylformamide solution, reducing the soluti...

Embodiment 3

[0031] A kind of synthetic method of mesalazine medicine intermediate 5-aminosalicylic acid, comprises the steps:

[0032] A. In a reaction vessel equipped with a stirrer and a reflux condenser, add 0.78mol of azobenzene salicylic acid, 200ml of sodium sulfite solution with a mass fraction of 20%, and 2-hydroxyl-5-methyl with a mass fraction of 31%. - 130ml of 3-nitropyridine solution, control the stirring speed at 110rpm, slowly add 0.83mol of molybdenum chloride powder, control the addition time at 2h, raise the solution temperature to 75°C, and react for 6h;

[0033] B, add mass fraction and be 160ml of xylene solution of 162%, reduce solution temperature to 10 ℃, separate out solid, recrystallize in the cyclohexanone solution that is 45% in 600ml mass fraction, obtain needle crystal, use 500ml mass fraction as Dissolve 21% oxalic acid solution, decolorize with molecular sieve, filter, add 200ml of N-methylformamide solution with a mass fraction of 65% to the filtrate, redu...

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Abstract

The invention discloses a synthesis method of a mesalazine drug intermediate 5-aminosalicylic acid. The method includes: in a mixed solution of sodium sulfite and 2-hydroxy-5-methyl-3-nitropyridine, subjecting azobenzene salicylic acid and molybdenum chloride to heating reflux reaction, then adding a xylene solution, conducting cooling, solid precipitation and recrystallization, using an oxalic acid solution to perform dissolving, and carrying out molecular sieve decoloration, filtration, cooling filtration and dehydration, thus obtaining 5-aminosalicylic acid. Compared with the synthesis method of the background technology, the method provided by the invention has obviously shortened reaction time and greatly improved reaction yield. Also, the invention provides a new synthetic route, and lays a good foundation for further improving reaction yield.

Description

technical field [0001] The invention relates to a preparation method of a pharmaceutical intermediate, belonging to the field of organic synthesis, in particular to a synthesis method of 5-aminosalicylic acid, a mesalazine pharmaceutical intermediate. Background technique [0002] Mesalamine drugs can inhibit the synthesis of prostaglandins that cause inflammation and the formation of inflammatory mediator leukotrienes, thereby significantly inhibiting the inflammation of intestinal mucosa. Mesalamine can inhibit prostaglandin synthesis and reduce PGE2 release in human colonic mucosa in a dose-dependent manner. Mesalazine can also inhibit the lipoxygenase activity of neutrophils. Adding mesalamine to culture human colonic mucosal cells can produce dose-effect inhibition on two important inflammatory mediators-chemotactic LTB4 and leukotrienes. At high doses, mesalazine can inhibit certain functions of human neutrophils, such as migration, degranulation, phagocytosis and sy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C229/64C07C227/04
CPCC07C227/04C07C229/64
Inventor 廖如佴
Owner 海宁经开产业园区开发建设有限公司
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