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Process for synthesizing 2-indolyone

A technology for indolinone and aniline, which is applied in the field of synthesizing 2-indolone, can solve the problems of low yield, complex process, short process flow and the like, and achieves the effects of high yield, easily available raw materials and simple process flow

Inactive Publication Date: 2008-01-16
BOHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0020] The raw materials in the above methods 1, 2, 3, 7, and 8 are not easy to obtain and the price is also expensive, the yield is not good, and it is not suitable for industrialized large-scale production
Although methods 5 and 6 use relatively cheap and easy-to-get aniline and o-nitrotoluene as raw materials respectively, their reaction process is long, the process is complicated, and the yield is low.
Although method 4 has a short technological process, its yield in the second step is only 44.7%

Method used

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  • Process for synthesizing 2-indolyone
  • Process for synthesizing 2-indolyone
  • Process for synthesizing 2-indolyone

Examples

Experimental program
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Effect test

Embodiment 1

[0031] Aniline and sodium hydroxide are put into a reaction kettle equipped with a constant pressure dripping device and a stirring device, and the molar ratio of the aniline and sodium hydroxide is 1.0: 2.0 to 1.0. Then add a solvent in the reaction kettle, the solvent is acetone or chloroform or ethyl acetate or ether, the amount of solvent added is based on the normal stirring of the reactants during the reaction. Then add chloroacetyl chloride into the constant pressure dropping device, the molar ratio of chloroacetyl chloride to aniline is 2.0~1.0:1.0. Under strong stirring, keep 0°C-25°C to slowly drop chloroacetyl chloride. Monitor the progress of the reaction with a TLC plate, and stop the reaction when the aniline reaction is complete. Evaporate the solvent under reduced pressure, then add water, the amount of water added is 2 / 3 to 5 / 6 of the volume of the reaction kettle, and extract with an organic solvent. The organic solvent can be extracted with ethyl acetate or...

Embodiment 2

[0034] Put aniline and sodium hydroxide in a reaction kettle equipped with a constant pressure dripping device and a stirring device, and the molar ratio of aniline and sodium hydroxide is 1.0:2.0. Then add a solvent in the reaction kettle, the solvent is acetone or chloroform or ethyl acetate or ether, the amount of solvent added is based on the normal stirring of the reactants during the reaction. Then add chloroacetyl chloride to the constant pressure dropping device, the molar ratio of chloroacetyl chloride to aniline is 2.0:1.0. Under strong stirring, keep 0°C-25°C to slowly drop chloroacetyl chloride. Monitor the progress of the reaction with a TLC plate, and stop the reaction when the aniline reaction is complete. Evaporate the solvent under reduced pressure, then add water, the amount of water added is 2 / 3 to 5 / 6 of the volume of the reaction kettle, and extract with an organic solvent. The organic solvent can be extracted with ethyl acetate or chloroform or ether. A...

Embodiment 3

[0037] Put aniline and sodium hydroxide in a reaction kettle equipped with a constant pressure dripping device and a stirring device, and the molar ratio of aniline and sodium hydroxide is 1.0:1.0. Then add a solvent in the reaction kettle, the solvent is acetone or chloroform or ethyl acetate or ether, the amount of solvent added is based on the normal stirring of the reactants during the reaction. Then add chloroacetyl chloride into the constant pressure dropping device, the molar ratio of chloroacetyl chloride to aniline is 1.0:1.0. Under strong stirring, keep 0°C-25°C to slowly drop chloroacetyl chloride. Monitor the progress of the reaction with a TLC plate, and stop the reaction when the aniline reaction is complete. Evaporate above-mentioned solvent under reduced pressure, then add water, the addition of water is 2 / 3~5 / 6 of reaction kettle volume, extract with organic solvent, described organic solvent can adopt ethyl acetate or trichloromethane or ether, The extract ...

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Abstract

The invention relates to a method to compounding 2-molindone that includes the following steps: using aniline as raw material, adding NaOH that the mol ratio is 1.0:2.0-1.0, adding solvent, taking reaction with chloroacetic chloride to form acylation material of aniline, and the mol ratio of chloroacetyl chloride is 2.0-1.0:1.0; according to the weight ratio of Lewis acid catalyst, chloride, and aniline is 7.0-4.0:1.0:1.0, whisking and heating to 120-220 degree centigrade, adding aniline and acylation material, controlling the reacting temperature at 180degree centigrade to 240 degree centigrade for 30-90min; adding cold water into the result of the reaction, and adding muriate acid to adjust the pH value, using organic solvent to distill and concentrate, and column chromatography separation to gain 2-molindone, the yield is 88.3%, and the melting point is 125.4-125.7 degree centigrade.

Description

Technical field: [0001] The invention relates to a method for synthesizing 2-indolinone by using aniline as raw material. Background technique: [0002] 2-indolinone itself is a drug for treating psychosis, and its structure type is different from several domestic drugs for treating psychosis, and its toxic and side effects are relatively mild. However, indolinone is more researched as a pharmaceutical intermediate, as a synthetic production of 2-indolinone compound with anti-inflammatory, antibacterial and analgesic effects. Recent studies have shown that 2-indolinone derivatives can inhibit HIV virus in cells, which opens up a new way for the development of prevention and treatment of AIDS. Its derivatives can also be used to prevent and treat the death of mammalian nerve cells caused by neurodegeneration, epilepsy, cerebral ischaemia, traumatic nerve cell damage, paralysis and spinal injury. It has been reported in the literature that 3-substituted indolones have antitu...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/34
Inventor 高文涛孟凡磊常明琴孙曙光
Owner BOHAI UNIV
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