Preparation method of indole-3-methanol

A technology for indole and methanol, applied in the field of preparation of indole-3-methanol, can solve the problems of difficult separation of reducing agents, increase in preparation cost and high preparation cost, achieve easy separation and regeneration, reduce preparation cost and improve reaction degree Effect

Inactive Publication Date: 2016-12-21
叶芳
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, most of the preparation methods of indole-3-carbinol use indole-3-carbaldehyde as raw material, and indole-3-carbinol is obtained by reducing indole-3-carbinaldehyde with different reducing agents in different reaction systems. The problem is that the separation of the reducing agent is difficult, which increases the preparation cost; most of the preparation methods of indole-3-carbaldehyde use indole and N,N-dimethylformamide as raw materials to react under the action of phosphorus oxychloride. into, average yield
However, the yield of this synthesis method is general, and it is difficult to separate the solvent medical alcohol from the product, and the preparation cost is relatively high

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Indole-3-carbinol was synthesized according to the following steps:

[0027] (1) Add dichloromethane into the reaction flask in the ice-water bath under the protection of nitrogen, start stirring, add zirconium chloride, then add tetrahydrofuran dropwise within 30 minutes, continue stirring for 1 hour, then add diethylamine and cyclopentadiene , the mass ratio of dichloromethane, zirconium chloride, tetrahydrofuran, diethylamine, and cyclopentadiene is 2.47:1.45:3.87:1:1.02, continue stirring for 2 hours, then heat to 45°C for reflux reaction for 7 hours, and cool to room temperature Afterwards, the product obtained is suction filtered, the filter cake is repeatedly washed with formic acid and then suction filtered again, and the obtained filter cake is recrystallized with chloroform to obtain zirconocene dichloride;

[0028] (2) Add montmorillonite to distilled water, heat to 70°C and stir for 10 minutes to obtain a montmorillonite solution with a concentration of 1.25...

Embodiment 2

[0034] Indole-3-carbinol was synthesized according to the following steps:

[0035] (1) Add dichloromethane into the reaction flask in the ice-water bath under the protection of nitrogen, start stirring, add zirconium chloride, then add tetrahydrofuran dropwise within 30 minutes, continue stirring for 1 hour, then add diethylamine and cyclopentadiene , the mass ratio of dichloromethane, zirconium chloride, tetrahydrofuran, diethylamine, and cyclopentadiene is 2.47:1.45:3.87:1:1.02, continue stirring for 2 hours, then heat to 45°C for reflux reaction for 7 hours, and cool to room temperature Afterwards, the product obtained is suction filtered, the filter cake is repeatedly washed with formic acid and then suction filtered again, and the obtained filter cake is recrystallized with chloroform to obtain zirconocene dichloride;

[0036] (2) Add montmorillonite to distilled water, heat to 70°C and stir for 10 minutes to obtain a montmorillonite solution with a concentration of 1.25...

Embodiment 3

[0042] Indole-3-carbinol was synthesized according to the following steps:

[0043] (1) Add dichloromethane into the reaction flask in the ice-water bath under the protection of nitrogen, start stirring, add zirconium chloride, then add tetrahydrofuran dropwise within 30 minutes, continue stirring for 1 hour, then add diethylamine and cyclopentadiene , the mass ratio of dichloromethane, zirconium chloride, tetrahydrofuran, diethylamine, and cyclopentadiene is 2.47:1.45:3.87:1:1.02, continue stirring for 2 hours, then heat to 45°C for reflux reaction for 7 hours, and cool to room temperature Afterwards, the product obtained is suction filtered, the filter cake is repeatedly washed with formic acid and then suction filtered again, and the obtained filter cake is recrystallized with chloroform to obtain zirconocene dichloride;

[0044] (2) Add montmorillonite to distilled water, heat to 70°C and stir for 10 minutes to obtain a montmorillonite solution with a concentration of 1.25...

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PUM

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Abstract

The invention provides a preparation method of indole-3-methanol. The method comprises the following steps: 1, carrying out a reaction on zirconium chloride and cyclopentadiene in a mixed solvent through a diethylamine technology to prepare zirconocene dichloride; 2, modifying montmorillonite with cystine to obtain modified montmorillonite; 3, compounding the modified montmorillonite with zirconocene dichloride to obtain montmorillonite supported zirconocene dichloride; 4, compounding the modified montmorillonite with potassium borohydride to obtain montmorillonite supported potassium borohydride; 5, carrying out an acylation reaction on indole and toluidine under the action of the montmorillonite supported potassium borohydride to obtain indole-3-formaldehyde; and 6, reducing the indole-3-formaldehyde by the montmorillonite supported potassium borohydride to prepare the indole-3-methanol. The method has the advantages of high yield and low preparation cost.

Description

technical field [0001] The invention relates to the field of pharmaceutical intermediates, in particular to a preparation method of indole-3-carbinol. Background technique [0002] Indole-3-carbinol is a natural food ingredient of cruciferous vegetables, which can inhibit the occurrence of tumors in many organs of the body, and also has a certain chemopreventive effect on cancer, and can reverse the multidrug resistance of tumors. Indole-3-carbinol is an important pharmaceutical intermediate. At present, most of the preparation methods of indole-3-carbinol use indole-3-carbaldehyde as raw material, and indole-3-carbinol is obtained by reducing indole-3-carbinaldehyde with different reducing agents in different reaction systems. The problem is that the separation of the reducing agent is difficult, which increases the preparation cost; most of the preparation methods of indole-3-carbaldehyde use indole and N,N-dimethylformamide as raw materials to react under the action of p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/12B01J31/22
CPCC07D209/12B01J31/2295B01J2231/4205B01J2531/0225B01J2531/48
Inventor 叶芳
Owner 叶芳
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