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Prepn process of 7-ethyl tryptophol

A technology of ethyl tryptophan and glycol ether, which is applied in the direction of organic chemistry, can solve the problems of high production cost, complicated process, and low reaction yield, and achieve the effects of convenient operation, good yield, and high product purity

Inactive Publication Date: 2006-03-01
杭州科本药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In order to overcome the shortcomings of low reaction yield, high production cost and complicated process in the prior art, the invention provides a kind of preparation method of 7-ethyl tryptophan

Method used

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  • Prepn process of 7-ethyl tryptophol
  • Prepn process of 7-ethyl tryptophol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] The preparation of embodiment 1 7-ethyltryptol

[0019] In a 500 mL reaction flask, add 70 grams of 2,3-dihydrofuran and 350 grams of ethylene glycol monomethyl ether, stir well, and set aside.

[0020] In another 1500mL reaction flask, add 350 grams of ethylene glycol monomethyl ether, 18 grams of water, and 173 grams of o-ethylphenylhydrazine hydrochloride, heat to 80 ° C, and then, the above-mentioned 2,3-dihydro The ethylene glycol monomethyl ether solution of furan was added dropwise to the reaction solution. After the addition was completed, the reaction was carried out for 6 hours. The ethylene glycol monomethyl ether was concentrated and evaporated, and 600 grams of water and 300 grams of dichloromethane were added. After stirring and layering, the Concentrate dichloromethane, distill under reduced pressure, collect fractions: 180-200°C (5mmHg), obtain 106 grams of light yellow solid, melting point: 55-62°C, purity: 91.8% (GC), pure yield: 51.6% .

Embodiment 2～12

[0022] Change the raw material consumption and the condition of reaction shown in embodiment 1, thus the product result that obtains is as shown in table 1.

[0023]

Embodiment 13-20

[0025] Change the kind of glycol ether solvent, others are all the same as embodiment 1, and reaction result is as shown in table 2.

[0026]

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Abstract

The preparation process of 7-ethyl tryptophol includes the following steps: reacting hydrolyzing 2, 3-dihydrofuran and o-ethyl phenylhydrazine hydrohcloride under the action of water inside glycol-ether solvent at the temperature from ¿C20 deg.c to solvent boiling point; and post-treatment. The 7-ethyl tryptophol preparing process of the present invention has high yield, convenient operation and high product purity, and is suitable for industrial production. The product is used in further production of etodolac.

Description

(1) Technical field [0001] The invention relates to a preparation method of 7-ethyl tryptophan. (2) Background technology [0002] 7-Ethyl tryptol is the key intermediate of the non-steroidal anti-inflammatory drug raw material etodolac, and its synthesis method can be via: (1) 2,3-dihydrofuran in dioxane at room temperature, Hydrazine hydrochloride is formed into a hydrazone, and then reacted at 95°C. It is separated and purified by chromatographic column (US4585877). (2) Ethylene glycol di-(tetrahydrofuryl) ether is mixed with o-ethyl phenylhydrazine hydrochloride reaction (JP58192867), (3) o-ethylaniline under the catalysis of cadmium sulfate, high temperature, and ethylene glycol cyclization 7-ethyl indole; then substituted by chloroacetyl chloride, Lithium hydride reduction derived (CA 1149396). [0003] Among the above-mentioned methods, method (1) has a low reaction yield and is separated and purified by column chromatography, which is not suitable for industrial pr...

Claims

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Application Information

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IPC IPC(8): C07D209/12
Inventor 游金宗蒋善会
Owner 杭州科本药业有限公司
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