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Preparation method of 3-amino-2-indolinone derivative promoted by iodine-hydrogen peroxide at room temperature

A technology of indolinone and derivatives, applied in the field of amination of 2-indolinone compounds, can solve the problems of high reaction cost and harsh reaction conditions, and achieve the effect of wide application range

Active Publication Date: 2018-08-24
NINGBO UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in these methods reported in the prior art, the reaction conditions are generally harsh and the reaction cost is high, for example, expensive catalytic systems such as noble metal rhodium and nitrogen ligands are required, and / or strong acids such as perchloric acid are used

Method used

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  • Preparation method of 3-amino-2-indolinone derivative promoted by iodine-hydrogen peroxide at room temperature
  • Preparation method of 3-amino-2-indolinone derivative promoted by iodine-hydrogen peroxide at room temperature
  • Preparation method of 3-amino-2-indolinone derivative promoted by iodine-hydrogen peroxide at room temperature

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1 compound Synthesis

[0026] Add 0.2 mmol of 3-phenyl-2-indolinone, 0.4 mmol of pyrrolidine, and 0.04 mmol of I to a Schlenk reaction flask with a volume of 20 mL. 2 , 0.4mmol of H 2 o 2 and ethanol (2mL), the reaction flask was placed at room temperature and stirred under air atmosphere conditions, and the reaction process was monitored by TLC or GC until the raw material was completely reacted (8 hours), and the reaction solution after the reaction was completed was concentrated under reduced pressure. The residue was separated by column chromatography (elution solvent: ethyl acetate / petroleum ether) to obtain the target product 3-pyrrolidino-3-phenyl-2-indolone.

[0027] White solid (87% yield); 1 H NMR (400MHz, CDCl 3 )δ: 8.87(s, 1H), 7.56(d, J=8.0Hz, 2H), 7.33-7.20(m, 5H), 7.02(t, J=7.6Hz, 1H), 6.91(d, J=8.0 Hz, 1H), 2.68 (t, J=6.0Hz, 4H), 1.73 (t, J=7.6Hz, 4H); 13 C NMR (100MHz, CDCl 3 )δ: 179.2, 140.6, 139.4, 130.5, 128.6, 128.4, 127.8, 127.4, 1...

Embodiment 2

[0028] Embodiment 2 replaces I with catalyst tetrabutylammonium iodide 2 , all the other conditions are the same as in Example 1, and the target product yield is 21%.

Embodiment 3

[0029] Embodiment 3 replaces I with catalyst potassium iodide 2 , all the other conditions are the same as in Example 1, and the target product yield is 32%.

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Abstract

The invention provides a preparation method of a 3-amino-2-indolinone derivative. The preparation method is simple in process, economical and green. According to the method, 2-indolinone compound 1a and alkylamine 2a are taken as raw materials and subjected to amination reaction under the conditions of I2-H2O2 system at room temperature, and the 3-amino-2-indolinone derivative I with high yield isprepared simply. The reaction formula of the derivative is as follows in the description.

Description

technical field [0001] The invention relates to a method for the amination of 2-indolinone compounds under a metal-free green catalytic system of iodine-hydrogen peroxide at room temperature, in particular to a method for amination of 2-indolinone compounds and alkylamines in I 2 -H 2 o 2 The amination reaction occurs under the system and at room temperature to prepare the method for obtaining 3-amino-2-indolinone derivatives. Background technique [0002] The development of green and efficient catalytic oxidation systems is a research hotspot in organic chemistry. As an ideal substitute for transition metal catalytic oxidation systems, the iodine-hydrogen peroxide system continues to show people its economical and green advantages. On the one hand, iodine is cheap, non-toxic, easy to obtain, and can be applied to many organic reactions. On the other hand, hydrogen peroxide is a safe and efficient oxidizing agent whose only by-product is water, which is harmless to the en...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/40
CPCC07D209/40
Inventor 高乐涵魏文廷包雯慧徐旭东汪依宁
Owner NINGBO UNIV
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