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Preparation method of isatoic anhydride derivative

A technology for isatoic anhydride and derivatives, which is applied in the field of preparation of isatoic anhydride derivatives, can solve the problems of harsh reaction conditions, cumbersome steps in the synthesis method, and limited source of raw materials, etc., and achieves a simple preparation method and a suitable environment for substrates , the effect of great application potential

Inactive Publication Date: 2015-11-11
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The reported synthetic methods generally have cumbersome steps, limited sources of raw materials, and relatively harsh reaction conditions.

Method used

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Experimental program
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Effect test

Embodiment 1

[0019] Palladium acetate (0.01mmol), copper pivalate (0.08mmol), and potassium iodide (0.04mmol) were added to the Schlenk reaction tube, and the system was replaced three times under an atmosphere of carbon monoxide / oxygen (molar ratio 1:1) at an atmospheric pressure. Then the substrate N,N-dimethylaniline (0.2mmol) and acetonitrile (2.0mL) were added in sequence to stop the reaction at 60°C for 48 hours, and 20mL of dichloromethane and 20mL of saturated potassium carbonate aqueous solution were added to the reaction system for extraction and separation to obtain The organic phase was then extracted once more with 20 mL of dichloromethane. The organic phases were combined, dried with anhydrous sodium sulfate, and separated by column chromatography to obtain isatoic anhydride derivatives with a separation yield of 70% and a purity of more than 95% by NMR. The characterization data are as follows:

[0020] NMR data: 1 HNMR (400MHz, CDCl 3 )δ7.98(d, J =8.5Hz,1H),7.60(dd, J ...

Embodiment 2

[0022] Palladium acetate (0.01mmol), copper pivalate (0.08mmol) and potassium iodide (0.04mmol) were added to the Schlenk reaction tube, and the system was replaced three times under a carbon monoxide / oxygen atmosphere at an atmospheric pressure. Then add the substrate N,N-diethyl-p-toluidine (0.2mmol) and acetonitrile (2.0mL) in turn to stop the reaction at 80°C for 40 hours, add 20mL dichloromethane and 20mL saturated potassium carbonate aqueous solution to the reaction system for extraction The organic phase was separated and extracted once more with 20 mL of dichloromethane. The organic phases were combined, dried with anhydrous sodium sulfate, and separated by column chromatography to obtain isatoic anhydride derivatives with a separation yield of 65% and a purity of more than 95% by NMR.

Embodiment 3

[0024] Palladium acetate (0.01mmol), copper pivalate (0.08mmol) and potassium iodide (0.04mmol) were added to the Schlenk reaction tube, and the system was replaced three times under a carbon monoxide / oxygen atmosphere at an atmospheric pressure. Then the substrate 3,4-dimethyl-N,N-dimethylaniline (0.2mmol) and acetonitrile (2.0mL) were added successively to stop the reaction at 70°C for 50 hours, and 20mL of dichloromethane and 20 mL of saturated potassium carbonate aqueous solution was extracted and separated to obtain an organic phase, and then extracted once with 20 mL of dichloromethane. The organic phases were combined, dried with anhydrous sodium sulfate, and separated by column chromatography to obtain isatoic anhydride derivatives with a separation yield of 69% and a purity of more than 95% by NMR.

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Abstract

The invention discloses a preparation method of an isatoic anhydride derivative. The preparation method comprises the following steps: in the presence of a palladium catalyst and a copper catalyst, dissolving N,N-dialkyl substituted arylamine and a catalytic amount of an inorganic salt in an organic solvent, and mixing uniformly; and then reacting for 40-55 hours in an atmosphere with a mixed gas of carbon monoxide and oxygen at 60-80 DEG C, and purifying to obtain the isatoic anhydride derivative. The preparation method is simple, the raw material, namely N,N-dialkyl substituted arylamine which is simple and easily available is used for constructing and synthesizing the isatoic anhydride derivative by one step, the preparation condition is mild, and the target product can be highly-selectively obtained in the atmosphere with the mixed gas of carbon monoxide and oxygen at 60 DEG C. The catalytic amount of the inorganic salt is used in the method to create a very good substrate applicable atmosphere, so that the range of a substrate is greatly expanded, the preparation of an isatoic anhydride compound with a practical value is realized, and the preparation method has a very great application potential in the aspect of drug synthetic intermediates and natural products.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a preparation method of isatoic anhydride derivatives. Background technique [0002] Amine compounds are a kind of simple and easy-to-obtain raw materials for industrial production. Many amine compounds are biologically active, and many natural products, drugs and dyes are also synthesized through amine compounds. Isatoic anhydride is the core structural unit of some drug molecules. Direct functionalization of hydrocarbons ortho to the amino group is interesting and challenging. The direct use of aromatic amines to synthesize isatoic anhydride through amino-ortho hydrocarbon esterification is a highly atom-economical method. So far, there is no relatively effective method for synthesizing these compounds. The reported synthetic methods generally have cumbersome steps, limited sources of raw materials, and relatively harsh reaction conditions. Contents of the inv...

Claims

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Application Information

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IPC IPC(8): C07D265/24
CPCC07D265/24
Inventor 雷爱文李武
Owner WUHAN UNIV
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