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Method for preparing indole compound and application thereof

An aniline compound and compound technology are applied in the field of organic synthesis, can solve the problems of cumbersome steps and high production costs, and achieve the effects of simple steps, convenient operation and reasonable route design.

Inactive Publication Date: 2017-12-08
CHONGQING HUAGE BIOCHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the current chemical synthesis methods have problems such as cumbersome steps and high production costs.

Method used

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  • Method for preparing indole compound and application thereof
  • Method for preparing indole compound and application thereof
  • Method for preparing indole compound and application thereof

Examples

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Effect test

preparation example Construction

[0016] The embodiment of the present invention provides a preparation method of indole compounds, which comprises:

[0017] S1. Reacting the aniline compound and ethylene oxide under the action of the first catalyst to obtain N-hydroxyethylaniline compound.

[0018] Aniline compounds are a common class of chemical raw materials. They come from a wide range of sources and are cheap and easy to obtain. Using them as raw materials can achieve the purpose of reducing costs. The oxygen in ethylene oxide has a strong electron-pulling effect, which makes the two carbons in ethylene oxide show a certain degree of electropositivity, and the ring tension of the three-membered ring makes ethylene oxide easy to be The nucleophile attacks and opens the ring. The aniline compound is reacted with oxirane, and the amino group of the aniline compound acts as a nucleophilic group to attack the oxirane to open the ring to form an N-hydroxyethylaniline compound. Among them, the structural formu...

Embodiment 1

[0031] This embodiment provides a kind of N-hydroxyethylaniline compound, and its reaction formula is

[0032]

[0033] Its preparation method is:

[0034] Weigh 10mmol of aniline and 0.1mmol of ZnCl in the reaction flask 2 , dissolved in 100ml of acetonitrile, and added 50mmol of ethylene oxide into the reaction flask at -20°C. Maintain -20°C and stir the reaction for 20h. After separation and purification, N-hydroxyethylaniline was obtained (yield 87.3%).

Embodiment 2

[0036] This embodiment provides a kind of N-hydroxyethylaniline compound, and its reaction formula is

[0037]

[0038] Its preparation method is:

[0039] Weigh 10mmol of 2-methylaniline and 0.2mmol of AlCl in the reaction flask 3 , dissolved in 100ml of tetrahydrofuran, at 0°C, add 30mmol of ethylene oxide into the reaction flask. Maintain 0°C and stir the reaction for 10h. After separation and purification, N-hydroxyethyl-2-methylaniline was obtained (yield 83.1%).

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Abstract

The invention provides a method for preparing an indole compound and application thereof, and relates to the field of organic synthesis. The preparation method comprises the following steps: reacting an aniline compound with ethylene oxide in the presence of a first catalyst to obtain an N-hydroxy ethylaniline compound; and reacting the N-hydroxy ethylaniline compound with the aniline compound in the presence of a second catalyst to prepare the indole compound. The preparation method has simple steps, can be used for preparing the indole compound with high efficiency and high yield by only two reacting steps, is reasonable in route design, simple in steps, convenient to operate and low in cost, and is suitable for industrial large-scale production. When the preparation method is applied to preparation of a medicine having an indole structure, the medicine yield can be improved, and large-scale production of the medicine can be promoted.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a preparation method and application of indole compounds. Background technique [0002] Indole and its derivatives are important organic raw materials and chemical products, which are widely used in the preparation of pesticides, medicines, dyes, spices, plant growth regulators and feed additives. With the further development and research of its derivatives, its application field is expanding rapidly, which makes the market demand for it continues to rise, especially the wide application of its derivative tryptophan in medicine and feed additives, making it popular in the world The annual demand exceeds 100,000 tons. However, the current global annual production capacity of indole is less than 10,000 tons, and its industrialization technology is mainly monopolized by industrialized countries and regions such as the United States, Western Europe, and Japan. [0003] At present, ...

Claims

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Application Information

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IPC IPC(8): C07D209/08
CPCC07D209/08
Inventor 何小强陈志忠吴承丽
Owner CHONGQING HUAGE BIOCHEM
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