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Preparation method of 3-nitroso-2-phenyl-1H-indole

A nitroso and phenyl technology, applied in the field of organic chemical synthesis, can solve problems such as low yield, environmental pollution, and increased reaction risk coefficient, and achieve the effects of high yield, short synthesis process, and low raw material cost

Inactive Publication Date: 2018-06-29
ASTATECH CHENGDU BIOPHARM CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The product yield is low by this method; the nitrous acid and acetic acid mixed system used will increase the risk factor of the reaction; and in the preparation process, a large amount of polluting gases such as nitrogen monoxide and nitrogen dioxide will be produced, which will easily cause environmental pollution

Method used

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  • Preparation method of 3-nitroso-2-phenyl-1H-indole
  • Preparation method of 3-nitroso-2-phenyl-1H-indole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] A preparation method of 3-nitroso-2-phenyl-1H-indole:

[0027] At 20ˉ30°C, tetrahydrofuran (500g) was added to a three-necked flask, and then 2-[2-(1-methyl-2-phenyl-1H-indol-3-yl)azo]benzothiazole ( 50g, 1.0eq) was added in the there-necked flask, stirred to dissolve completely; Potassium hydroxide (15.2g, 2.0eq) was added to 50g of water to prepare aqueous potassium hydroxide solution;

[0028] At 0°C, add potassium hydroxide aqueous solution dropwise to the reaction system in the three-necked flask, and after the dropwise addition, raise the temperature of the system to 50-60°C and react for 8ˉ10h. After the reaction is over, cool down the reaction system to 0-10°C;

[0029] Slowly add 10% dilute hydrochloric acid dropwise to the above reaction system, adjust the pH value of the system to 1-2, separate the organic phase, extract the product with methyl tert-butyl ether (500g) in the water phase, combine the organic phase, add water (250g) and stir to wash Organic p...

Embodiment example 2

[0031] A preparation method of 3-nitroso-2-phenyl-1H-indole:

[0032] At 20ˉ30°C, tetrahydrofuran (500g) was added to a three-necked flask, and then 2-[2-(1-methyl-2-phenyl-1H-indol-3-yl)azo]benzothiazole ( 50g, 1.0eq) was added in the there-necked flask, stirred to dissolve completely; sodium hydroxide (10.9g, 2.0eq) was added to 50g of water to prepare aqueous sodium hydroxide solution;

[0033] At 0°C, add the sodium hydroxide aqueous solution dropwise to the reaction system in the three-necked flask. After the dropwise addition, raise the temperature of the system to 50-60°C and react for 8ˉ10h. After the reaction is over, cool down the reaction system to 0-10°C;

[0034] Slowly add 10% dilute hydrochloric acid dropwise to the above reaction system, adjust the pH value of the system to 1-2, separate the organic phase, extract the product with methyl tert-butyl ether (500g) in the water phase, combine the organic phase, add water (250g) and stir to wash Organic phase, liq...

Embodiment example 3

[0036] At 20ˉ30°C, acetonitrile (500g) was added to a three-necked flask, and then 2-[2-(1-methyl-2-phenyl-1H-indol-3-yl)azo]benzothiazole ( 50g, 1.0eq) was added in the there-necked flask, stirred to dissolve completely; Potassium hydroxide (15.2g, 2.0eq) was added to 50g of water to prepare aqueous potassium hydroxide solution;

[0037] At 0°C, add potassium hydroxide aqueous solution dropwise to the reaction system in the three-necked flask, and after the dropwise addition, raise the temperature of the system to 50-60°C and react for 8ˉ10h. After the reaction is over, cool down the reaction system to 0-10°C;

[0038] Slowly add 10% dilute hydrochloric acid dropwise to the above reaction system, adjust the pH value of the system to 1-2, separate the organic phase, extract the product with methyl tert-butyl ether (500g) in the water phase, combine the organic phase, add water (250g) and stir to wash Organic phase, liquid separation, add anhydrous sodium sulfate (100g) to the...

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Abstract

The invention discloses a preparation method of 3-nitroso-2-phenyl-1H-indole, and belongs to the field of organic chemical synthesis. The preparation method comprises the following steps of using 2-[2-(1-methyl-2-phenyl-1H-indole-3-ox)azo]benzothiazole as the raw material; dissolving, and adding alkaline to react; after reaction is completed, adjusting the pH (potential of hydrogen) value to 1 to2, separating liquid, extracting, concentrating, cooling and crystallizing, filtering, and drying, so as to obtain a 3-nitroso-2-phenyl-1H-indole product. The preparation method has the advantages that by using 2-[2-(1-methyl-2-phenyl-1H-indole-3-ox)azo]benzothiazole and alkaline, and various reagents as the raw materials, the prices are low, and the raw materials are easy to obtain; the technology steps are fewer, the operation is simple, the safety and environment-friendly effect are good, the total yield rate is high, and the preparation method is suitable for industrialized production.

Description

technical field [0001] The invention relates to the field of organic chemical synthesis, in particular to a preparation method of 3-nitroso-2-phenyl-1H-indole. Background technique [0002] In 1935, Campbell and Cooper reported a method of synthesizing 3-nitroso-2-phenyl-1H-indole in the literature "Journal of the Chemical Society, 1935, 1208-1211". This method uses 1- Methyl-2-phenylindole was used as starting material to prepare 3-nitroso-2-phenyl-1H-indole by using nitrous acid and acetic acid mixed system. The product yield is low by this method; the nitrous acid and acetic acid mixed system used will increase the reaction risk factor; and a large amount of nitrogen monoxide, nitrogen dioxide and other polluting gases will be produced in the preparation process, which will easily cause environmental pollution. The reaction formula is as follows: [0003] Contents of the invention [0004] The object of the present invention is to: aim at the above-mentioned existi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/30
CPCC07D209/30
Inventor 罗建业李显军郭鹏
Owner ASTATECH CHENGDU BIOPHARM CORP
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