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Preparation method for 1-aryl-2-indolinone derivatives

A technology of indolinone and its derivatives, applied in the direction of organic chemistry, etc., can solve the problems of expensive raw materials, few reports on synthetic methods, high reaction temperature, etc., and achieve the effect of cheap raw materials, low cost and simple operation

Active Publication Date: 2013-09-11
中国人民解放军防化学院
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Problems solved by technology

The literature reports the synthetic method of a large amount of indole compounds, but, for the synthetic method report of 1-aryl-2-indolinone derivative, the most important method is to adopt Friedel-Crafts reaction method to construct indole Ketone ring structure (see Figure 1)
This method has disadvantages such as high reaction temperature and expensive raw materials.

Method used

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  • Preparation method for 1-aryl-2-indolinone derivatives
  • Preparation method for 1-aryl-2-indolinone derivatives
  • Preparation method for 1-aryl-2-indolinone derivatives

Examples

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Embodiment 1

[0020] (a) the preparation of N-(2,6-dichlorophenyl) phenylacetamide (III-a)

[0021] method one:

[0022] Add 16.20g (0.1mol) of 2,6-dichloroaniline and 9.49g (0.12mol) of pyridine to a 250ml three-neck flask equipped with a thermometer, constant pressure dropping funnel, reflux condenser and anhydrous calcium chloride drying tube. and 100ml acetone. After stirring, cooling in an ice-water bath, 15.45 g (0.1 mol) of phenylacetyl chloride was slowly added dropwise. After the addition was complete, the ice-water bath was removed. Heating, reflux 4h. Stop responding.

[0023] The reaction solution was poured into 250ml of 1.5mol / L hydrochloric acid solution while hot, and a large amount of yellow blocky solid appeared. The solid was filtered off and washed successively with 100ml×2 3mol / L hydrochloric acid solution, 100ml×2 1mol / L NaOH solution, and 100ml×2 deionized water. After drying, a yellow solid was obtained. 26.50 g of white needle-like crystals were obtained by r...

Embodiment 2

[0062] (a) Preparation of N-(4-chlorophenyl) phenylacetamide (III-b)

[0063] Using p-chloroaniline and phenylacetyl chloride as raw materials, N-(4-chlorophenyl)phenylacetamide (III-b) was prepared according to the first method of Example 1 (a), and finally 23.95 g of white needle-like crystals were obtained. The yield 96.3%. Melting point: 161.5-163.9°C

[0064] (b) Preparation of N-chloro-N-(4-chlorophenyl) phenylacetamide (II-b)

[0065] Taking N-(4-chlorophenyl) phenylacetamide (III-b) as raw material, prepare N-chloro-N-(4-chlorophenyl) phenylacetamide (II- b) Finally, 27.98 g of light yellow solid was obtained, and the yield was about 100%.

[0066] (c) Preparation of 1-(4-chlorophenyl)-2-indolinone (I-b)

[0067] Using N-chloro-N-(4-chlorophenyl)phenylacetamide (II-b) as raw material, prepare 1-(4-chlorophenyl)-2-dihydroindoline according to method 1 of Example 1(c) Indolin ketone (I-b), 17.61 g of a light yellow solid was finally obtained, with a yield of 72.3%. ...

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Abstract

The invention discloses a method for synthesis of 1-aryl-2-indolinone derivatives. The method comprises the following steps: dissolving N-aryl-substituted phenylacetamide (III) in an organic solvent, adding a chlorination reagent and carrying out a reaction so as to obtain N-chloro-N-aryl-substituted phenylacetamid (II); and subjecting N-chloro-N-aryl-substituted phenylacetamid to a reaction with a certain amount of Lewis acid and a proper amount of an organic solvent at a certain temperature so as to obtain 1-aryl-2-indolinone (I). The method provided by the invention has the advantages of simple operation, easily available reagents, a low price, mild conditions and capability of synthesizing a plurality of 1-aryl-2-indolinone (I) compounds.

Description

technical field [0001] The present invention relates to a preparation method of 1-aryl-2-indolinone derivatives. Background technique [0002] 1-aryl-2-indolinone derivatives have important application value and research significance in the fields of medicine and chemical synthesis. It can be used as an important intermediate to synthesize a variety of chemical products and drugs, such as non-steroidal anti-inflammatory drugs such as diclofenac. The literature reports the synthetic method of a large amount of indole compounds, but, for the synthetic method report of 1-aryl-2-indolinone derivative, the most important method is to adopt Friedel-Crafts reaction method to construct indole Ketone ring structure (see Figure 1). This method has disadvantages such as high reaction temperature and expensive raw materials. Contents of the invention [0003] The object of the present invention is to provide a method for synthesizing 1-aryl-2-indolinone derivatives (I) with readily...

Claims

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Application Information

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IPC IPC(8): C07D209/34
Inventor 任丽君田兴涛向玉联樊启平陈虹黄志平周蕾
Owner 中国人民解放军防化学院
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