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Prepn process of 7-ethyl tryptophol

A technology of ethyl tryptophan and ethyl, which is applied in the field of preparation of 7-ethyl tryptophan, can solve the problems of high production cost, complicated process and low reaction yield, and achieve the advantages of convenient operation, good yield and high product purity Effect

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

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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

[0021] The preparation of embodiment 1 7-ethyl tryptophan

[0022] In a 500mL reaction flask, add 350g of ethylene glycol monomethyl ether, 18g of water, and 10g of concentrated hydrochloric acid, below 0°C, add 70g of 2,3-dihydrofuran dropwise, and stir for 1 hour after the addition is complete. ,stand-by.

[0023] In another 1500mL reaction flask, add 350 grams of ethylene glycol monomethyl ether and 173 grams of o-ethylphenylhydrazine hydrochloride, and heat to 80°C under stirring. Then, the above-mentioned ethylene glycol monomethyl ether The solution was slowly added dropwise to the reaction solution containing o-ethylphenylhydrazine hydrochloride, after the addition was completed, reacted for 8 hours, concentrated and evaporated to remove ethylene glycol monomethyl ether, added 600 grams of water, 300 grams of dichloromethane, stirred and separated Afterwards, dichloromethane was concentrated, distilled under reduced pressure, and fractions were collected: 180-200°C (5m...

Embodiment 2～12

[0025] The raw material consumption and conditions of the reaction shown in Example 1 were changed, so that the product results obtained are shown in Table 1.

[0026] Example

Embodiment 13-20

[0028] Change the acid that adopts and its consumption, the kind of glycol ether solvent, others are all the same as embodiment 1, and reaction result is as shown in table 2.

[0029]

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Abstract

The preparation process of 7-ethyl tryptophol includes the following steps: hydrolyzing 2, 3-dihydrofuran inside glycol-ether solvent to obtain 4-hydroxy butyraldehyde; reacting 4-hydroxy butyraldehyde and o-ethyl phenylhydrazine hydrohcloride inside glycol-ether solvent in the temperature from ¿C20 deg.c to solvent boiling point for 1-24 hr; 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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