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Preparation method of 3-hydroxy-3-(4-hydroxy-2-oxo-2-hydrogen-chromene-3-yl)indolin-2-one

An indoline and hydroxyl technology, applied in the field of organic compound synthesis, can solve problems such as complicated operation and complicated reaction apparatus, and achieve the effects of simple operation, high yield and mild conditions

Inactive Publication Date: 2017-08-29
ZUNYI MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Method 2 (Journal of The Electrochemical Society, 159(11)G123-G127(2012)): It is obtained by reacting isatin derivatives with 4-hydroxycoumarin under electrolytic conditions. The required reaction equipment is relatively complicated and the operation is cumbersome

Method used

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  • Preparation method of 3-hydroxy-3-(4-hydroxy-2-oxo-2-hydrogen-chromene-3-yl)indolin-2-one
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  • Preparation method of 3-hydroxy-3-(4-hydroxy-2-oxo-2-hydrogen-chromene-3-yl)indolin-2-one

Examples

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Effect test

Embodiment 1

[0017] Example 1: Preparation of 3-hydroxyl-3-(4-hydroxyl-2-oxo-2-hydrogen-chromene-3-yl)-5-fluoroindoline-2-one (I-1)

[0018] Add 5-fluoroisatin (1mmol), 4-hydroxycoumarin (1.05mmol), tetrabutylammonium bromide (0.1mmol) and water (4mL) into a microwave reaction tube, microwave power 400W, and irradiate at 70°C for 10min , stop the microwave radiation, cool to room temperature, filter under reduced pressure, wash the filter cake with ice ethanol (0.5ml), and dry under reduced pressure to obtain a white solid with a yield of 96%.

[0019] 1 H NMR (CDCl 3 )δ: 10.48(s, 1H), 7.92(d, 1H, J=8.0Hz), 7.68~7.63(m, 2H), 7.43~7.36 (m, 3H), 7.16(d, 1H, J=8.0Hz ),7.08~7.03(m,1H),6.83~6.80(m,1H); 13 C NMR (CDCl 3 )δ: 176.07, 165.55, 160.07, 157.25, 152.69, 139.56, 133.39, 133.15, 132.85, 132.78, 124.82, 116.30, 116.17, 110.91, 100.66, 91.43.

Embodiment 2

[0020] Example 2: Preparation of 3-hydroxyl-3-(4-hydroxyl-2-oxo-2-hydrogen-chromen-3-yl)-7-fluoroindoline-2-one (I-2)

[0021] Add 7-fluoroisatin (1 mmol), 4-hydroxycoumarin (1.1 mmol), tetrabutylammonium chloride (0.1 mmol) and water (4 mL) into a microwave reaction tube, microwave power 400W, and irradiate at 60°C for 15 min , stop the microwave radiation, cool to room temperature, filter under reduced pressure, wash the filter cake with ice ethanol (0.5ml), and dry under reduced pressure to obtain a white solid with a yield of 94%.

[0022] 1 H NMR (CDCl 3 )δ:10.99(s,1H),7.92(d,1H,J=8.0Hz),7.69~7,65(m,2H),7.43~7.34(m,3H),7.19~7.14(m,1H) ,7.11~7.09(m,1H),6.94~6.91(m,1H); 13 C NMR (CDCl 3 )δ: 175.83, 165.39, 160.10, 152.65, 133.48, 124.91, 124.36, 123.02, 120.37, 117.49, 117.32, 116.81, 100.87, 91.44, 78.65.

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Abstract

The invention relates to the field of organic synthesis and particularly relates to a preparation method of 3-hydroxy-3-(4-hydroxy-2-oxo-2-hydrogen-chromene-3-yl)indolin-2-one (I). An isatin derivative and a 4-hydroxycoumarin derivative as raw materials undergo a reaction under co-catalysis of a phase transfer catalyst and microwave to produce a compound I. The preparation method has the advantages of mild conditions, simple operation and high yield.

Description

technical field [0001] The present invention relates to the technical field of organic compound synthesis, in particular to the preparation method of 3-hydroxyl-3-(4-hydroxyl-2-oxo-2-hydrogen-chromen-3-yl) indoline-2-one (I) . Background technique [0002] The preparation method of 3-hydroxyl-3-(4-hydroxyl-2-oxo-2-hydrogen-chromen-3-yl) indoline-2-ketone (I), the reported synthetic method mainly contains two kinds: [0003] Method 1 (Acta Cryst. (2011). E67, o307): obtained by reacting 4-bromoisatin and 4-hydroxycoumarin under the catalysis of benzyltriethylammonium chloride, the reaction time is longer and the yield is higher Low. [0004] Method 2 (Journal of The Electrochemical Society, 159(11)G123-G127(2012)): It is obtained by reacting isatin derivatives with 4-hydroxycoumarin under electrolytic conditions, and the required reaction equipment is relatively complicated and the operation is cumbersome. Contents of the invention [0005] The present invention provides...

Claims

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Application Information

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IPC IPC(8): C07D405/04
CPCC07D405/04
Inventor 张磊王京刘来郑诚月王杨
Owner ZUNYI MEDICAL UNIVERSITY
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