Method of using deep eutectic solvent to prepare 2-arylindole compounds

A technology of deep eutectic solvent and arylindole, which is applied in the direction of organic chemistry, can solve the problems of many synthesis steps, pollute the environment, and complex raw materials, and achieve the effect of simple synthesis, environmental friendliness, and easy-to-obtain raw materials

Active Publication Date: 2016-12-07
XINZHOU TEACHERS UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The purpose of the present invention is to solve the technical problems of complex raw materials, many synthesis steps, low yield and environmental pollution in the existing preparation method of 2-arylindole compounds, and provide a deep eutectic solvent as solvent and catalyst, Method for preparing 2-arylindole compounds by one-step reaction of phenylhydrazine and substituted acetophenone

Method used

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Examples

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Comparison scheme
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Embodiment 1

[0013] A method for preparing 2-arylindole compounds using a deep eutectic solvent in this embodiment comprises the following steps:

[0014] (1) Preparation of deep eutectic solvent: the zinc chloride ZnCl of 0.01mol choline chloride ChCl and 0.04mol 2 Mix, slowly raise the temperature to 95°C, and stir magnetically at a constant temperature at 95°C for 8 hours to obtain the deep eutectic solvent ChCl+4ZnCl 2 ;

[0015] (2) Preparation of 2-arylindole compounds: sequentially add 0.01mol of the deep eutectic solvent ChCl+4ZnCl prepared in step (1) 2 , 0.01mol of phenylhydrazine and 0.01mol of 4-chloroacetophenone were added to the reaction vessel, the reaction mixture was magnetically stirred for 70min at a temperature of 120°C, and the reaction was stopped. After the reaction was cooled to room temperature, it was stirred with water, and filtered under reduced pressure. The filter cake is washed to neutrality with 10% polyphosphoric acid to obtain a white crude product, and...

Embodiment 2

[0017] A method for preparing 2-arylindole compounds using a deep eutectic solvent in this embodiment comprises the following steps:

[0018] (1) Preparation of deep eutectic solvent: the zinc chloride ZnCl of 0.01mol choline chloride ChCl and 0.04mol 2 Mix, slowly raise the temperature to 100°C, and stir magnetically at a constant temperature at 100°C for 12 hours to obtain the deep eutectic solvent ChCl+4ZnCl 2 ;

[0019] (2) Preparation of 2-arylindole compounds: sequentially add 0.01mol of the deep eutectic solvent ChCl+4ZnCl prepared in step (1) 2 , 0.01mol of phenylhydrazine and 0.01mol of 4-chloroacetophenone were added to the reaction vessel, the reaction mixture was magnetically stirred at a temperature of 125°C for 90 minutes, and the reaction was stopped. After the reaction was cooled to room temperature, it was stirred with water, and suction filtered under reduced pressure. The filter cake is washed to neutrality with 10% polyphosphoric acid to obtain a white cr...

Embodiment 3

[0021] A method for preparing 2-arylindole compounds using a deep eutectic solvent in this embodiment comprises the following steps:

[0022] (1) Preparation of deep eutectic solvent: the zinc chloride ZnCl of 0.01mol choline chloride ChCl and 0.04mol 2 Mix, slowly raise the temperature to 98°C, and magnetically stir at a constant temperature at 98°C for 10 hours to obtain the deep eutectic solvent ChCl+4ZnCl 2 ;

[0023] (2) Preparation of 2-arylindole compounds: sequentially add 0.01mol of the deep eutectic solvent ChCl+4ZnCl prepared in step (1) 2 , 0.01mol of phenylhydrazine and 0.01mol of 4-chloroacetophenone were added to the reaction vessel, the reaction mixture was magnetically stirred for 80min at a temperature of 123°C, and the reaction was stopped. After the reaction was cooled to room temperature, it was stirred with water, and filtered under reduced pressure. The filter cake is washed to neutrality with 10% polyphosphoric acid to obtain a white crude product, an...

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PUM

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Abstract

The invention discloses a method of using a deep eutectic solvent to prepare 2-arylindole compounds, and relates to the technical field of organic compound preparation. The deep eutectic solvent is environment-friendly and is taken as the reaction solvent and catalyst. 2-arylindole compounds are prepared through one-step reactions between phenyl hydrazine and substituted acetophenone. The method comprises the following steps: mixing choline chloride (ChCl) and zinc chloride (ZnCl2) according to a mole ratio of 1:4, slowly heating to a temperature of 95 to 100 DEG C, maintaining the temperature, stirring the mixture by magnetic force for 8 to 12 hours to obtain a deep eutectic solvent (ChCl+4ZnCl2); sequentially adding the prepared deep eutectic solvent, phenyl hydrazine, and substituted acetophenone into a reactor according to a mole ratio of 1:1:1, magnetically stirring the mixture for 70 to 90 minutes at a temperature of 120 to 125 DEG C, after reactions, cooling to the room temperature, adding water, stirring, carrying out vacuum suction filtration, washing the filter cake by polyphosphoric acid (10%) until the filter cake becomes neutral to obtain a coarse product, and further recrystallizing the coarse product by ethanol (95%) to obtain a pure crystalline product. The synthesis method is simple, the raw materials are easily available, the cost is low, and the method can be applied to massive production.

Description

technical field [0001] The invention belongs to the technical field of preparation methods of organic compounds, and in particular relates to a method for preparing 2-arylindole compounds through one-step reaction using a deep eutectic solvent as a solvent and a catalyst. Background technique [0002] Indole and its derivatives are a class of heterocyclic compounds that widely exist in nature, and are also important organic raw materials and chemical products. They are widely used in research fields such as pharmacy, agricultural chemistry, and material science. The synthesis methods of indole ring include phenylhydrazine method, aniline method, o-aminoethylbenzene method, ortho-chlorotoluene method, etc., but the most widely used method is the most convenient and economical phenylhydrazine synthesis method. The classic phenylhydrazine method is completed by a two-step reaction: the first step is to condense aliphatic aldehydes, ketones and phenylhydrazine derivatives into c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/10
CPCC07D209/10
Inventor 赵三虎夏志卿贾晓丽范建凤
Owner XINZHOU TEACHERS UNIV
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