Method for preparing 3-(4-methoxyphenyl)-succinimide

A technology of succinimide and methoxyphenyl, applied in the field of preparation of succinimide compounds, can solve the problems of long reaction route, excessive reaction route, harsh reaction conditions and the like, and achieves easy industrial production, The effect of simple reaction operation and shortened reaction time

Inactive Publication Date: 2014-07-23
DONGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among the above three synthetic methods, the reaction route of the first synthetic method and the second method is too long, and there are many by-products
The third method, phenylboronic acid, is more expensive, and microwave heating is used in the reaction, which is not suitable for large-scale synthesis
[0003] In summary, the above method has the disadvantages of long reaction route, low yield and harsh reaction conditions, and the cost is relatively high in large-scale production.

Method used

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  • Method for preparing 3-(4-methoxyphenyl)-succinimide
  • Method for preparing 3-(4-methoxyphenyl)-succinimide
  • Method for preparing 3-(4-methoxyphenyl)-succinimide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Take 54.1g (0.50mol) of anisole, 48.5g (0.50mol) of maleimide and 66.5g (0.5mol) of anhydrous aluminum trichloride and add them to a 1000mL round bottom flask, add 600mL of dichloroethane, Heat, stir and reflux for 8 hours. After the reaction is completed, add 500 mL of 2N hydrochloric acid to the reaction solution, stir for 10 minutes, filter with suction, and wash with water. The obtained solid is recrystallized with 95% ethanol to obtain 78.4 g of white solid, yield 76.5%, mp: 128 ~129°C.

Embodiment 2

[0034] Take 54.1g (0.50mol) of anisole, 48.5g (0.50mol) of maleimide and 133.0g (1.0mol) of anhydrous aluminum trichloride and add them to a 2000mL round bottom flask, add 600mL of dichloroethane, Heat, stir and reflux for 8 hours. After the reaction is complete, add 500 mL of 2N hydrochloric acid to the reaction solution, stir for 10 minutes, filter with suction, wash with water, and recrystallize the obtained solid with 95% ethanol to obtain 83.0 g of white solid, yield 81.0%, mp: 128~130°C .

Embodiment 3

[0036] Take 54.1g (0.50mol) of anisole, 97.0g (1.0mol) of maleimide and 133.0g (1.0mol) of anhydrous aluminum trichloride and add them to a 2000mL round bottom flask, add 800mL of dichloroethane, Heat, stir and reflux for 5 hours. After the reaction is complete, add 600 mL of 2N hydrochloric acid to the reaction solution, stir for 10 minutes, filter with suction, wash with water, and recrystallize the solid with 95% ethanol to obtain 88.5 g of white solid, yield 86.3%, mp: 128-130°C.

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Abstract

The invention relates to a method for preparing 3-(4-methoxyphenyl)-succinimide. The method comprises the following steps: dissolving anisole, maleimide and lewis acid into a solvent; heating and refluxing to react for 3-20 hours; adding 2N hydrochloric acid, stirring, filtering and recrystallizing to obtain 3-(4-methoxyphenyl)-succinimide. The 3-(4-methoxyphenyl)-succinimide prepared by the method has high yield, low price, simple reaction operation, short reaction route, less three-wastes, and easiness for realization of industrial production.

Description

technical field [0001] The invention belongs to the field of preparation of succinimide compounds, in particular to a preparation method of 3-(4-methoxyphenyl)succinimide. Background technique [0002] 3-(4-Methoxyphenyl)succinimide (I) and its derivatives are important drug synthesis intermediates, and have important curative effects in anticonvulsant, sedative, hypnotic, etc. (Miller, C.A.; Long , L.M.J. Am. Chem. Soc. 1951, 73, 4895-4899). The synthetic method of bibliographical information 3-(4-methoxyphenyl) succinimide mainly comprises three kinds: method one is to use p-methoxybenzaldehyde and ethyl α-cyanoacetate condensation, after passing through potassium cyanide A series of reactions such as addition and acidification to prepare 3-(4-methoxyphenyl)succinimide (I) (Miller, C.A.; Scholl, H.I.; Long, L.M.J.Am.Chem.Soc.1951,73 , 5608-5610, Miller, C.A.; Long, L.M.J.Am.Chem.Soc.1953, 75, 373-376. and Miller, C.A.; Long, L.M.J.Am.Chem.Soc.1953, 75, 6256-6258), method...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/40
CPCC07D207/40
Inventor 赵圣印安玉龙
Owner DONGHUA UNIV
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