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Method for preparing mecarbinate (1,2-dimethyl-5hydroxy-1H-indol-3-ethyl carboxylate)

A technology of mecabene ester and ethyl carboxylate, applied in the field of preparation of mecabene ester (1,2-dimethyl-5 hydroxy-1H-indole-3-carboxylate ethyl ester), can solve Problems such as poor product purity, high cost, and low yield, achieve the effects of low cost, short cycle, and low reaction temperature

Inactive Publication Date: 2013-05-22
SHAANXI PUCHENG WANDE SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The present invention is to solve the deficiency of the above-mentioned technical background, and provides a kind of preparation method of mecarbbenate (1,2-dimethyl-5-hydroxy-1H-indole-3-carboxylic acid ethyl ester), which overcomes the existing The technical yield is low, the cost is high, and the product purity is poor.

Method used

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  • Method for preparing mecarbinate (1,2-dimethyl-5hydroxy-1H-indol-3-ethyl carboxylate)
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  • Method for preparing mecarbinate (1,2-dimethyl-5hydroxy-1H-indol-3-ethyl carboxylate)

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Embodiment 1

[0025] Add 350g (3.24mol) of p-benzoquinone to 2100ml of dichloromethane, stir at room temperature, add 140g of zinc chloride, heat to 30℃, stir to dissolve completely, control the temperature at 30-35℃ and add 525g (3.67mol) dropwise ) A mixture of ethyl 3-methylamino-2-butenoate in 260ml of dichloromethane, drip in about 1 hour. After the addition is complete, stir and react for 1.5 hours at about 35°C, and then recover about 1400ml of dichloromethane Add 2800ml of 60% ethanol aqueous solution, stir at room temperature for 1 hour, filter, collect the solid, and dry to obtain 648g off-white solid product, yield 85.8%, product mp208-209°C, purity (HPLC) 98.75%. (See figure 1 )

[0026] 1 HNMR (CDCl 3 ,δppm ), 1.36 (t, 3H -CH3), 2.26 (S, 3H -CH3), 3.54 (S.3H-CH3), 4.35 (S.2H -CH2), 6.40-7.10 (m.3H Ar-H ).

[0027] IR(KBr,.cm -1 ) 3560, 3010, 2940, 2860, 1760, 1450, 1250, 1010, 810, 650,

Embodiment 2

[0029] Add 350g (3.24mol) of p-benzoquinone to 2100ml of 1,2-dichloroethane, stir at room temperature, add 140g of zinc chloride, heat to 30℃, stir to dissolve completely, control the temperature to 35-40℃ and add dropwise 525g (3.67mol) 3-methylamino-2-butenoic acid ethyl ester in 260ml, 1.2-dichloroacetic acid mixed solution, about 1 hour dripping, after the addition, control 35-40 ℃ stirring reaction for 1.5 hours, then control 40 About 1460ml of dichloroethane was recovered under reduced pressure at about ℃, added with 2800ml of 60% ethanol aqueous solution, stirred at room temperature for 1 hour, filtered, collected the solid, and dried to obtain an off-white solid product 642g, mp208-210℃. Yield 85.1%, purity ( HPLC) 98.61% (see figure 2 )

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Abstract

The invention relates to a method for preparing mecarbinate (1,2-dimethyl-5hydroxy-1H-indol-3-ethyl carboxylate). The obtained target object has the purity of over 98 percent and the yield of over 85 percent, and compared with the prior art, the method has the advantages that the reaction yield is high, the cost is reduced by about 28 percent, the reaction temperature is low, the period is short (the reaction temperature and the reaction time are shortened by a half), the energy is saved, and the method is high in safety, easy to operate, high in product purity and suitable for industrial production. According to the technical scheme, the method comprises the following steps: adding benzoquinone into a hydrochloric ether solvent, adding a Lewis acid catalyst, stirring at room temperature for dissolving, heating to control the temperature, dripping a mixture of 3-methylamino-2-ethyl crotonate and hydrochloric ether, continuously stirring and reacting for a certain time at the controlled temperature after dripping is finished, recovering the solvent, adding alcohol-water, stirring at the room temperature for one hour, filtering, collecting the solid and drying to obtain a white target product.

Description

1. Technical field: [0001] The invention relates to a preparation method of mecabenate (ethyl 1,2-dimethyl-5-hydroxy-1H-indole-3-carboxylate). 2. Background technology: [0002] The chemical name of mecabene ester is 1,2-dimethyl-5-hydroxy-1H-indole-3-carboxylic acid ethyl ester, which is an important pharmaceutical synthesis intermediate with a wide range of applications, especially antiviral drugs An essential intermediate in the synthesis of Arbidol hydrochloride. Its structural formula is as follows: [0003] [0004] In 1929, Romanian chemist Nenitzescu reported the method of synthesizing 5-hydroxyindole derivatives, but the synthesis yield was only 32%. Wu Xiuzheng's 2002 master's thesis and 2003 Song Yanling's master's thesis of Shenyang Medical University in my country, consulted a large number of domestic and foreign literature on this reaction, and conducted a review report and scientific experimental research, Fine and Specialty Chemicals 2007.15 (13) and Fin...

Claims

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Application Information

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IPC IPC(8): C07D209/42
CPCY02P20/121
Inventor 刘立强
Owner SHAANXI PUCHENG WANDE SCI & TECH
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