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Method for one-step constructing 2-tertiary butyl-4-methoxy isoindolin-1,3-diketone by utilizing imine as initial raw material

A methoxyisoindoline, tert-butyl technology, applied in the fields of biology, medicine and life science, can solve the problems of low yield, poor separation effect, etc., achieve excellent yield, mild reaction conditions, and increase practicability Effect

Inactive Publication Date: 2019-01-18
GUILIN UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Its classic synthetic route is Gabriel synthetic method, and this method takes phthalimide salt and alkylating reagent as reaction raw material, needs to react in highly polar aprotic solvent, and yield is low , the separation effect is poor

Method used

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  • Method for one-step constructing 2-tertiary butyl-4-methoxy isoindolin-1,3-diketone by utilizing imine as initial raw material
  • Method for one-step constructing 2-tertiary butyl-4-methoxy isoindolin-1,3-diketone by utilizing imine as initial raw material
  • Method for one-step constructing 2-tertiary butyl-4-methoxy isoindolin-1,3-diketone by utilizing imine as initial raw material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] In a 25mL test tube, add (E)-N-tert-butyl-1-(2-methoxyphenyl)methanimine 0.2 mmol, dichlorodiacetonitrile palladium 0.01 mmol, copper oxide 0.2 mmol, add Toluene and N,N-dimethylformamide were used as a mixed solvent with a volume ratio of 10:1, 0.2 mmol of water was added, and then a balloon containing carbon monoxide and oxygen was used as a carbonyl source, and stirred at 100 degrees Celsius for 24 hours. After the TLC (thin layer chromatography) detection reaction, the reaction solution was cooled to room temperature, the balloon was removed, and the unreacted carbon monoxide and oxygen were slowly vented. The reaction solution was filtered, the filtrate was evaporated under reduced pressure to remove the solvent, and then separated and purified by column chromatography to obtain the target product 2-tert-butyl-4-methoxyisoindoline-1,3-dione. The column layer used The eluent was a mixed solvent of petroleum ether:ethyl acetate with a volume ratio of 10:1, and the yi...

Embodiment 2

[0026] In a 25mL test tube, add (E)-N-tert-butyl-1-(2-methoxyphenyl)methanimine 0.2 mmol, dichlorodiacetonitrile palladium 0.01 mmol, copper oxide 0.2 mmol, add Toluene was used as a solvent, 0.2 mmol of water was added, and then a balloon containing carbon monoxide and oxygen was covered as a carbonyl source, and stirred at 100 degrees Celsius for 24 hours. TLC (thin layer chromatography) tracking detection, no target product was detected.

Embodiment 3

[0028] In a 25mL test tube, add (E)-N-tert-butyl-1-(2-methoxyphenyl)methanimine 0.2 mmol, dichlorodiacetonitrile palladium 0.01 mmol, copper oxide 0.2 mmol, add N,N-dimethylformamide was used as a solvent, 0.2 mmol of water was added, and then a balloon containing carbon monoxide and oxygen was used as a carbonyl source, and stirred at 100 degrees Celsius for 24 hours. TLC (thin layer chromatography) tracking detection, no target product was detected.

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Abstract

The invention discloses a method for one-step constructing 2-tertiary butyl-4-methoxy isoindolin-1,3-diketone by utilizing imine as an initial raw material. According to the method, (E)-N-tertiary butyl-1-(2-methoxy phenyl) methylenimine is taken as a reaction raw material and is subjected to carbonylation reaction, so as to one-step construct 2-tertiary butyl-4-methoxy isoindolin-1,3-diketone. The method has the characteristics of mild reaction conditions, simple operation process, and high yield.

Description

technical field [0001] The invention relates to the technical fields of biology, medicine and life science, and specifically relates to a method for constructing 2-tert-butyl-4-methoxyisoindoline-1,3-dione in one step by using imine as a starting material. Background technique [0002] N-hydrocarbyl phthalimide is an important class of fine chemical intermediates, which are widely used in the fields of medicine, polymer materials, dyes, etc. body. Therefore, the synthetic method about N-hydrocarbyl phthalimide has become a research focus of chemists at home and abroad. Its classic synthetic route is Gabriel synthetic method, and this method takes phthalimide salt and alkylating reagent as reaction raw material, needs to react in highly polar aprotic solvent, and yield is low , the separation effect is poor. Faced with such reaction limitations, the present invention uses imine as a starting material to construct 2-tert-butyl-4-methoxyisoindoline-1,3-dione in one step, whi...

Claims

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Application Information

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IPC IPC(8): C07D209/48
CPCC07D209/48
Inventor 及方华王守才
Owner GUILIN UNIVERSITY OF TECHNOLOGY
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