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Preparation method for N-phenyl indolone

A technology of phenylindolinone and diphenylacetamide, which is applied in the field of preparation of N-phenylindolinone, can solve problems such as high reaction temperature, potential safety hazards, complicated operation, etc., and achieve lower reaction temperature, large Industrial application value, safe and simple operation

Inactive Publication Date: 2018-09-04
SHANGHAI BETTERSYN BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In the Friedel-Crafts alkylation reaction, reagents such as aluminum trichloride are often used, and the amount of waste water is large, which is not friendly to the environment; secondly, the Friedel-Crafts alkylation reaction temperature is high, the operation is complicated, and there are potential safety hazards

Method used

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  • Preparation method for N-phenyl indolone
  • Preparation method for N-phenyl indolone
  • Preparation method for N-phenyl indolone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Dissolve 20g of diphenylamine (0.118mol) in 200mL of dichloromethane, add 23.9g of triethylamine (0.236mol, 2.0eq), lower the temperature to 0-5°C, and slowly add 16g of chloroacetyl chloride (0.142mol, 1.20 eq). After the dropwise addition, the temperature was raised to 25±5°C and stirred for 16 hours. 200mL of water was added, stirred and extracted, and the organic phase was dried and concentrated to obtain 26g of 2-chloro-N,N-diphenylacetamide (90% yield). TLC detected the product Rf = 0.65 (V n-heptane: V ethyl acetate = 4:1), melting point 118-120°C. 1 HNMR (400M, CDCl 3 )δ7.24~7.48, m, 10H; 4.05, s, 2H.

Embodiment 2

[0040] Dissolve 20g of diphenylamine (0.118mol) in 100mL of toluene, add 17.9g of triethylamine (0.177mol, 1.50eq), cool down to 0-5°C, and slowly add 14.6g of chloroacetyl chloride (0.130mol, 1.10eq ). After the dropwise addition, the temperature was raised to 80°C to keep the temperature, and stirred for 0.5 hours. Add 200mL of water, stir and extract, and the organic phase is dried and concentrated to obtain 24.4g (yield 84%). The result of structural identification is close to Example 1.

Embodiment 3

[0042] Dissolve 20g of diphenylamine (0.118mol) in 100mL of xylene, add 13.8g of sodium carbonate (0.130mol, 1.10eq), cool down to 0-5°C, and slowly add 14.6g of chloroacetyl chloride (0.130mol, 1.10eq ). After the dropwise addition, the temperature was raised to 80°C to keep the temperature, and stirred for 0.5 hours. Add 200mL of water, stir and extract, and the organic phase is dried and concentrated to obtain 26.6g (yield 92%). The result of structural identification is close to Example 1.

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Abstract

The invention especially relates to a preparation method for N-phenyl indolone, belonging to the field of organic synthesis. The preparation method for N-phenyl indolone comprises the following steps:subjecting diphenylamine (a compound as shown in a formula II) and chloroacetyl chloride (a compound as shown in a formula III) to a condensation reaction to prepare 2-chloro-N,N-diphenylacetamide (acompound as shown in a formula IV); subjecting 2-chloro-N,N-diphenylacetamide and acetate to an esterification reaction so as to obtain 2-acetoxy-N,N-diphenylacetamide (a compound as shown in a formula V); and subjecting 2-acetoxy-N,N-diphenylacetamide to a ring closure reaction so as to obtain N-phenyl indolone. The preparation method provided by the invention is a clean high-efficiency synthesis method for N-phenyl indolone; in the whole preparation process, high-contamination raw materials are discarded, and reaction temperature is lowered; and the method is friendly to environment and safe and simple to operate, and has great industrial application value.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a preparation method of N-phenylindolinone. Background technique [0002] N-phenylindolinone is an important pharmaceutical intermediate. At present, the synthesis method of N-phenylindolinone is mainly to obtain the intermediate 2-chloro-N,N-diphenylacetamide after reacting diphenylamine and chloroacetyl chloride, and then obtain the ring closure through Friedel-Crafts alkylation reaction, specifically The reaction equation is as follows: [0003] [0004] In the Friedel-Crafts alkylation reaction, reagents such as aluminum trichloride are often used, and the amount of waste water is large, which is not friendly to the environment. Secondly, the Friedel-Crafts alkylation reaction temperature is high, the operation is complicated, and there are potential safety hazards. Contents of the invention [0005] In view of the above-mentioned shortcomings of the prior art, the obj...

Claims

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Application Information

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IPC IPC(8): C07D209/34C07C231/12C07C235/16
CPCC07C231/02C07C231/12C07D209/34C07C233/07C07C235/16
Inventor 何其中王清山罗光顺
Owner SHANGHAI BETTERSYN BIOTECH