4-hydroxyindole preparation method suitable for industrial production

A technology of oxindole and indole, which is applied in the field of preparation of 4-oxindole and industrialized production, can solve the problems of high reaction temperature, harsh conditions, and high equipment requirements, and achieve simplified operation steps, mild reaction conditions, and high reaction yield. high rate effect
CN110423211AInactive Publication Date: 2019-11-08苏州楚凯药业有限公司
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Patent Information

Authority / Receiving Office
CN · China
Current Assignee / Owner
苏州楚凯药业有限公司
Publication Date
2019-11-08
Estimated Expiration
Not applicable · inactive patent

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Abstract

The invention relates to the technical field of organic synthesis, in particular to a preparation method of a medical intermediate 4-hydroxyindole. The method includes: taking 1, 5, 6, 7-tetrahydro-4H-indole-4-one as the raw material, carrying out nucleophilic substitution reaction under the action of alkali to obtain an amino protection product (I), reacting the compound (I) with a halogenation reagent to obtain alpha-halogenated ketone (II), subjecting the compound (II) to elimination reaction under the action of alkali to remove HX so as to obtain a 4-hydroxyindole derivative (III), and finally conducting hydrolysis deprotection on the compound (III) to obtain 4-hydroxyindole (IV). The invention provides a simple industrial production route for 4-hydroxyindole, and the method has the advantages of simple reaction operation, avoidance of high temperature, high pressure and catalytic reaction, and low cost.
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Description

Technical field

[0001] The invention belongs to the technical field of organic synthesis, and specifically relates to a preparation method of 4-hydroxyindole suitable for industrial production. Background technique

[0002] Hydroxyindoles are raw materials for the synthesis of many natural compounds. Among the many discovered natural products and pharmaceutically active compounds, indole often serves as a significant structural unit. Therefore, it is necessary to obtain new synthesis of this skeleton with different substitution forms. Methods are the main goal of current organic synthesis.

[0003] Indole derivatives such as hydroxyindole are also important organic chemical raw materials and pharmaceutical intermediates. They can be used to synthesize dyes, spices and some drugs, and can also be used as plant auxins, feed additives, etc. In particular, 4-hydroxyindole is an important intermediate in the synthesis of the angina treatment drug Pindolol (Pindolol) and the psyc...

Claims

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