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A kind of method for preparing 1-phenylindole

A technology of phenylindole and phenylindolinone, which is applied in the field of synthesizing 1-phenylindole, a key intermediate of iminostilbene, and synthesizing 1-phenylindole, can solve the need for column chromatography, original Expensive excipients, unsafe production factors, etc., to achieve the effect of optimizing reaction conditions

Inactive Publication Date: 2016-06-08
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] In order to solve the above problems, that is, the raw materials are expensive, there are unsafe factors in production, and purification requires column chromatography, etc., the present invention provides a low-cost, high-safety, high-stability synthesis of 1-phenylindole easy way

Method used

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  • A kind of method for preparing 1-phenylindole
  • A kind of method for preparing 1-phenylindole
  • A kind of method for preparing 1-phenylindole

Examples

Experimental program
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Effect test

example 1

[0026] (1) Add 20.9 g (0.1 mol) of N-phenylindolinone and 200 mL of cyclohexane into a four-neck flask, stir, and heat to reflux.

[0027] (2) Add 10.78g (0.2mol) of potassium borohydride and 1.33g (0.01mol) of aluminum chloride in batches, react for 11-24 hours, and track the reaction by TLC. After the reaction, cool slightly, filter, add an appropriate amount of water to the organic layer to quench, filter to obtain the filtrate, separate the liquids to obtain the organic layer, dry over anhydrous magnesium sulfate, filter, and recover the solvent by rotary evaporation under reduced pressure to obtain 12.54 g of 1-phenylindole , yield 64.97%.

example 2

[0029] (1) Add 20.9g (0.1mol) of N-phenylindolinone and 400mL of toluene into a four-neck flask, stir and heat to reflux.

[0030] (2) Add 11.4g (0.3mol) of sodium borohydride and 11.1g (0.1mol) of calcium chloride in batches, react for 11-24 hours, and track the reaction by TLC. After the reaction, cool slightly, filter, quench the organic layer with an appropriate amount of water, filter to obtain the filtrate, separate the liquids to obtain the organic layer, dry over anhydrous magnesium sulfate, filter, and recover the solvent by rotary evaporation under reduced pressure to obtain 17.17g of 1-phenylindole , yield 88.96%.

example 3

[0032] (1) Add 20.9g (0.1mol) of N-phenylindolinone and 600mL of tetrahydrofuran into a four-necked flask, stir, and heat to reflux.

[0033] (2) Add 19g (0.5mol) of sodium borohydride and 13.6g (0.1mol) of zinc chloride in batches, react for 11-24 hours, and track the reaction by TLC. After the reaction, cool slightly, filter, quench the organic layer with an appropriate amount of water, filter to obtain the filtrate, separate the liquids to obtain the organic layer, dry over anhydrous magnesium sulfate, filter, and recover the solvent by rotary evaporation under reduced pressure to obtain 18.49 g of 1-phenylindole , yield 95.80%.

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Abstract

The invention relates to a method for preparing 1-phenylindole, belonging to the field of organic synthesis. The method for preparing the 1-phenylindole takes N-phenylindole ketone or N-phenyl isatin as a starting material, complex metal hydride in an organic solvent as a reducing agent and lewis acid as a catalyst, and the 1-phenylindole can be obtained by reflux reaction. The method has the positive progress effects that a more novel method for synthesizing the 1-phenylindole is provided by the invention, the reaction conditions are optimized, the reducing agent and the solvent can be recycled, and the yield reaches up to more than 95%, so that the method has a certain research value.

Description

technical field [0001] The present invention relates to a kind of method of the key intermediate 1-phenylindole of synthetic iminostilbene, relate in particular to a kind of with N-phenylindolinone and N-phenylisatin as starting raw material, in reducing agent and The method for synthesizing 1-phenylindole under the action of a catalyst belongs to the field of organic synthesis. Background technique [0002] 1-Phenylindole is an important pharmaceutical intermediate and fine chemical product. The structure is shown in Formula 1: [0003] [0004] Structural Formula 11-Phenylindole [0005] There are many existing patents and bibliographical reports in the synthesis of this compound, wherein more classic is exactly Fischer indole (organic chemistry, 2006,26 (8): 1025-1030; ApplCatalA:General, 2005,292:305-311; JKoreanChemSoc, 2010,54(4):411-413; TetrahedronLett,2008,49:984-986.) Synthetic method, the basic principle is to use aliphatic aldehydes, ketones and phenylhydra...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/08
CPCC07D209/08
Inventor 宋国强唐龙冯筱晴曹引梅陈鹏魏涛沈梦笔郭文驿孟凯成
Owner CHANGZHOU UNIV
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