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2,5-dihydroxy-n-(2-hydroxyethyl)benzamide preparation method

A technology of gentisic acid ethanolamine and ethanolamine is applied in the preparation of carboxylic acid amides, the preparation of organic compounds, chemical instruments and methods, etc., and can solve the problems of difficult purification of reaction products, difficult operation of synthesis process, difficulty in separation and purification of final products, and the like, To achieve the effect of reducing cost and environmental pollution, easy availability of raw materials and improving quality

Inactive Publication Date: 2013-04-03
北京京卫信康医药科技发展有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Method 1 has high activity because gentisic acid is converted into acid chloride, and it is easy to obtain by-products when reacting with ethanolamine, and the separation and purification of the final product is difficult; method 2 also makes the reaction product difficult to purify due to the introduction of a condensing agent; method 3 uses chlorine Ethyl formate activates gentisic acid, because ethyl chloroformate has a strong pungent smell, making the synthesis process difficult to operate

Method used

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  • 2,5-dihydroxy-n-(2-hydroxyethyl)benzamide preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Add 200g of methyl gentisate into a 500ml single-necked bottle, drop in 79.9g of ethanolamine, heat slightly, wait until the solids are completely dissolved, raise the temperature to 80°C, keep stirring for 8 hours, monitor by TLC, until the reaction is complete, dissolve with 200ml of purified water, overnight Crystallize, filter with suction, wash with water twice, and dry under vacuum at 50°C for 4 hours to obtain 160.6 g of the product with a yield of 68.44%.

[0023] Spectral data for structural confirmation of the product: 1 H NMR (400MHz, DMSO-d 6 )δ: 3.33 ~ 3.36 (m, 2H, -CH 2 -), 3.49~3.53(m, 2H, -CH 2 -), 4.74~4.76(m, 1H, -OH), 6.71~6.73(d, 1H, =CH-), 6.82~6.84(d, 1H, =CH-), 7.25(s, 1H, =CH- ), 8.67(s, 1H, 1H, -OH), 8.95(s, 1H, -OH), 11.57(s, 1H, -NH-), the results are consistent with the structure.

Embodiment 2

[0025] Add 200g of methyl gentisate into a 1000ml single-necked bottle, and then add 200ml of water; raise the temperature to 80°C, add 79.9g of ethanolamine dropwise, keep stirring for 8 hours, monitor by TLC, until the reaction is complete, dissolve in 200ml of purified water, and crystallize overnight. Suction filtration, washing with water twice, and vacuum drying at 50° C. for 4 hours gave 170.0 g of the product with a yield of 72.44%. The structure of the product was confirmed to be consistent.

Embodiment 3

[0027] Add 200g of ethyl gentisate into a 1000ml single-necked bottle, and then add 200ml of water; raise the temperature to 80°C, add 79.9g of ethanolamine dropwise, keep stirring for 8 hours, monitor by TLC, until the reaction is complete, dissolve in 200ml of purified water, and crystallize overnight. Suction filtration, washing with water twice, and vacuum drying at 50° C. for 4 hours gave 150.0 g of the product with a yield of 63.92%. The structure of the product was confirmed to be consistent.

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Abstract

The present invention relates to a 2,5-dihydroxy-N-(2-hydroxyethyl)benzamide preparation method, wherein gentisate and ethanolamine are subjected to a condensation reaction to prepare the 2,5-dihydroxy-N-(2-hydroxyethyl)benzamide. The method has characteristics of simple operation, reduced cost and reduced environmental pollution.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, in particular to a preparation method of ethanolamine gentisate. Background technique [0002] The chemical name of gentisic acid ethanolamine is 2,5-dihydroxy-N-(2-hydroxyethyl)benzamide, because gentisic acid ethanolamine has a chelating effect on metal ions, it is used as a complexing agent and Antioxidant synergists, for example, can be used in the preparation of injections and sterile liquid preparations, and can be used as intermediates in the synthesis of flecainide raw materials in the pharmaceutical field. [0003] The structure of ethanolamine gentisate is: [0004] [0005] The synthetic method of prior art gentisic acid ethanolamine is mainly the following methods, method 1: first convert gentisic acid into acid chloride, and then obtain amidation reaction with ethanolamine; method 2: use gentisic acid in the presence of a condensation agent (condensing Mixtures such as: 2-chlo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C235/60C07C231/02
Inventor 曹志华胡军常迪刘烽张勇
Owner 北京京卫信康医药科技发展有限公司
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