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Synthesis method of constructing isatoic anhydride and isatoic anhydride derivative by one step by utilizing carbonylation reaction

A technology of carbonylation reaction and isatoic anhydride, which is applied in the field of medicinal chemistry, can solve the problems of environmental friendliness, personal safety and production equipment damage, and achieve the effect of high step economy, efficient and convenient synthesis means, simple and safe operation

Active Publication Date: 2017-10-27
山东诺缘商贸有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The chloroformate and phosgene used in these two methods are highly toxic raw materials, and a large amount of corrosive gas hydrogen chloride will also be generated during the reaction. Therefore, from the perspective of green chemistry, the above methods are not environmentally friendly. Cause certain damage to personal safety and production equipment

Method used

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  • Synthesis method of constructing isatoic anhydride and isatoic anhydride derivative by one step by utilizing carbonylation reaction
  • Synthesis method of constructing isatoic anhydride and isatoic anhydride derivative by one step by utilizing carbonylation reaction
  • Synthesis method of constructing isatoic anhydride and isatoic anhydride derivative by one step by utilizing carbonylation reaction

Examples

Experimental program
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Effect test

Embodiment 1

[0034] Add 0.2 mmol of N,N-dimethylaniline, 0.01 mmol of palladium chloride, 0.2 mmol of copper acetate into a 25 mL test tube, add toluene (PhMe) and N,N-dimethylformamide (DMF)3 mL as a mixed solvent with a volume ratio of 10:1, put a balloon containing carbon monoxide and oxygen as a carbonyl source, and stir at 100 degrees Celsius. TLC (Thin Layer Chromatography) Detection After the 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, and the filtrate was rotary evaporated under reduced pressure to remove the solvent, and then separated and purified by column chromatography to obtain the target product with a yield of 27%.

Embodiment 2

[0036] In a 25mL test tube, add 0.2 mmol of N,N-dimethylaniline, 0.01 mmol of bistriphenylphosphine palladium dichloride, 0.2 mmol of copper acetate, add toluene (PhMe) and N,N-dimethyl 3 ml of formamide (DMF) was used as a mixed solvent with a volume ratio of 10:1, covered with a balloon containing carbon monoxide and oxygen as a carbonyl source, and stirred at 100 degrees Celsius. 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, and the filtrate was rotary evaporated under reduced pressure to remove the solvent, and then separated and purified by column chromatography to obtain the target product with a yield of 49%.

Embodiment 3

[0038] Add 0.2 mmol of N,N-dimethylaniline, 0.01 mmol of palladium dichlorodiacetonitrile, 0.2 mmol of copper acetate, add toluene (PhMe) and N,N-dimethylformamide (DMF ) 3 ml as a mixed solvent with a volume ratio of 10:1, put on a balloon containing carbon monoxide and oxygen as a carbonyl source, and stir at 100 degrees Celsius. 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, and the filtrate was rotary evaporated under reduced pressure to remove the solvent, and then separated and purified by column chromatography to obtain the target product with a yield of 68%.

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Abstract

The invention relates to a method of constructing isatoic anhydride and an isatoic anhydride derivative by one step by utilizing a carbonylation reaction. The method comprises the steps of adding N,N-dialkyl arylamine, a metal palladium catalyst and copper salt as an oxidant and a solvent to a reaction vessel, sleeving a balloon filled with carbon monoxide and oxygen on a reactor, performing a stirring reaction for 1-10h at 40-150 DEG C, performing cooling to a room temperature after reaction completion, dismounting the balloon, filtering a reaction liquid, performing reduced pressure evaporation to remove the solvent to obtain a crude product, and performing column chromatography purification to obtain isatoic anhydride and the isatoic anhydride derivative. The synthesis method of constructing isatoic anhydride and the isatoic anhydride derivative by the one step by utilizing the carbonylation reaction has the characteristics that operation is concise, raw materials are easy to obtain, the functional group tolerance is good, and a yield is excellent; and the method has an important research value on synthesis and preparation of isatoic anhydride and the isatoic anhydride derivative.

Description

technical field [0001] The invention relates to the technical fields of medicinal chemistry, pesticide science, dye chemistry, organic synthesis, etc., and specifically relates to a synthesis method for constructing isatoic anhydride and its derivatives in one step by utilizing carbonylation reaction. Background technique [0002] Isatoic anhydride and its derivatives are a class of organic heterocyclic compounds with wide application value. Due to their own structural characteristics, this kind of substance can be used as both an electrophile and a nucleophile, so it is a very important organic intermediate and has important research value in the fields of medicine, pesticides and dyes. [0003] At present, there are two commonly used methods for constructing the structural skeleton of isatoic anhydride, both of which use anthranilic acid as a reaction raw material. Cyclic two-step construction of isatoic anhydride. The second method is to use anthranilic acid and phosgen...

Claims

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Application Information

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IPC IPC(8): C07D265/26
CPCC07D265/26
Inventor 及方华
Owner 山东诺缘商贸有限公司
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