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A process for preparing isatin derivatives from substituted aniline

A technology for the preparation of aniline and derivatives, which is applied in the field of preparing isatin derivatives from substituted anilines, which can solve the problems of low yield of target compounds and non-separable isomeric products, avoiding the use of catalysts and ligands, and avoiding heavy metal pollution , the effect of short reaction cycle

Inactive Publication Date: 2019-05-21
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, when using substrates with ortho-substituted or electron-withdrawing substituents, these methods can lead to the formation of target compounds in low yields or to non-separable isomeric products

Method used

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  • A process for preparing isatin derivatives from substituted aniline
  • A process for preparing isatin derivatives from substituted aniline
  • A process for preparing isatin derivatives from substituted aniline

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Example 1 N-methyl-2-phenylaminoacetamide (I-a)

[0037] Add material II aniline (0.93g, 10mmol) and material III 2-chloro-N-methylacetamide (1.07g, 10mmol) into a 50mL single-necked bottle, and react in 50mL toluene at 70°C for 24h. After the reaction, it was cooled, poured into 100 mL of water, filtered, washed, and dried to obtain 1.55 g of solid product with a yield of 94.5% and a melting point of 162.0-163.2°C.

Embodiment 2

[0038] Embodiment 2 ethyl acetate (E)-2-(p-tolylamino) ester (I-b)

[0039] Add material II p-toluidine (1.07g, 10mmol) and material III ethyl glyoxylate (1.02g, 10mmol) into a 50mL single-necked bottle, and react in 50mL xylene at room temperature for 24h. After the reaction was completed, 1.56 g of solid product was obtained by distillation under reduced pressure, with a yield of 99.4% and a melting point of 162.3-164.8°C.

Embodiment 3

[0040] Example 3 5-fluoro-indoline-2,3-dione (I-c)

[0041] Add raw material II p-fluoroaniline (1.11g, 10mmol), raw material III N-phenyl-glycine isopropyl ester (3.86g, 20mmol) in 50mL one-mouth bottle, acid is pentafluoroacetic acid (3.28g, 20mmol), at 60 ℃ 100mL acetonitrile in the air for 16h. After the reaction, it was cooled, poured into 100 mL of water, filtered, washed and dried to obtain 1.30 g of solid product with a yield of 78.7% and a melting point of 222.2-224.5°C.

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Abstract

A process for preparing isatin derivatives from substituted aniline is provided. The process includes preparing isatin derivatives with a high yield from substituted aniline shown as a formula II anda carbonylation agent shown as a formula III through acid catalytic oxidation. Compared with traditional processes, the process has characteristics of cheap raw materials, simple and convenient operation, mild reaction conditions, a high product yield, high product purity, wide applicability, and the like, and is environmentally friendly. In addition, the process does not adopt a noble metal catalyst or ligand, so that heavy metal pollution is avoided and the process is suitable for industrial production.

Description

(1) Technical field [0001] The invention relates to a novel preparation method for preparing isatin derivatives by carbonylation of substituted anilines. (2) Background technology [0002] Isatin, also known as 2,3-diketone indoline, is an indole derivative and an important heterocyclic compound, with a ketone and lactam structure, and has biological activities, such as antibacterial, anti-tuberculosis, and anti-convulsant activities. important in chemistry. [0003] The compound was first discovered in the leaves and roots of Isatidis, and was isolated in 1840 from Radix Isatidis, Cannonball Fruit and Shrimp Ridge. These plants are very abundant in the northern and central regions of China and are of great value in traditional preparation methods. It is also found as a component of the parotid gland secretions of toad frogs and other organisms such as Caribbean tumorigenic plants, lichens, fungi, marine molluscs and humans, as it is a metabolic derivative of adrenaline. ...

Claims

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Application Information

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IPC IPC(8): C07D209/38C07D471/04C07D495/04
Inventor 李坚军周嘉第陈永健何云飞李中辉苏为科
Owner ZHEJIANG UNIV OF TECH