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Method for synthesizing indoline and derivates thereof

A technology of indoline and its derivatives, which is applied in the field of synthesis of indoline and its derivatives, can solve the problems of increasing production costs and expensive copper, and achieve the effects of cost saving, high product yield and easy recycling

Inactive Publication Date: 2008-12-24
NINGBO INST OF TECH ZHEJIANG UNIV ZHEJIANG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But its shortcoming is that the two (8-hydroxyquinoline) copper as catalyst is expensive, which increases the production cost

Method used

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  • Method for synthesizing indoline and derivates thereof
  • Method for synthesizing indoline and derivates thereof
  • Method for synthesizing indoline and derivates thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Embodiment 1 Add the 99% o-chlorophenethylamine of 15.6g (0.10mol) in the flask that electric stirrer, thermometer, condenser tube 100mL are housed, 30g20%NaOH (0.15mol) aqueous solution, the supported copper catalyst of 7.8g ( 10%Cu / TiO 2 ), reacted at 90°C for 8h. The reaction liquid was analyzed by gas chromatography mass spectrometry, and the result was 0.1% o-chlorophenethylamine, 0.8% indole, and 97.8% indoline. Separate the organic layer and the water layer, extract the water layer with 5 mL of chloroform, combine the chloroform layer and the organic layer, pickle with 5% hydrochloric acid, wash with water, and rectify to obtain 11.2 g of indoline (boiling point: 94 ~ 95 ° C / 11 mmHg). The yield is 94.0%, and the gas phase purity is 99.5%.

Embodiment 2

[0032] Embodiment 2 changed o-chlorophenethylamine into 21.4g (0.10mol) o-bromophenethylamine, and others were the same as in Example 1 to obtain 11.4g of product indoline with a yield of 95.7% and a gas phase purity of 99.6%.

Embodiment 3

[0033] In Example 3, the reaction time was changed to 5h, and the others were the same as in Example 1. The results were 1.5% o-chlorophenethylamine, 0.6% indole, 96.9% indoline, 92.5% yield, and 99.4% gas phase purity.

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PUM

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Abstract

The invention relates to a method for synthesizing indoline in formula (I) and a derivative thereof. Titanium dioxide laden copper of Cu / TiO2 with a charge number between 5 and 15 weight percent is taken as a catalyst. The a compound in formula (II) and the catalyst have condensation reaction under the action of a dehydrohalogenation agent to produce the indoline, wherein R1, R2, R3 and R4 represent hydrogen, C1 to C4 represent alkyl, C1 to C4 represent alkoxyl group and nitryl, and C1 to C4 represent hydroxyalkyl; and R5 represents hydrogen, and C1 and C2 represent alkyl. The method avoids the operation at high pressure, avoids the use of raw materials such as organic amine and the catalyst with high price and great toxicity, lowers the cost, improves the operating environment, is easy to reclaim the catalyst and has high yield of the product.

Description

technical field [0001] The invention relates to a synthesis method of indoline and its derivatives. Background technique [0002] Indoline and its derivatives widely exist in nature, and many indoline derivatives can be used as initial raw materials and intermediates of medicines, pesticides, spices, dyes, etc. At present, there are many methods for the synthesis of indoline. [0003] U.S. Patent US4087442, US4159271 have introduced such a synthetic route: take 2-chlorophenethylamine as raw material, metal copper, inorganic copper catalyst (copper chloride, copper sulfate, copper nitrate, cupric oxide), organic copper catalyst (copper oxalate, Copper catalysts such as copper acetate) and ammonia water as a dehydrohalogenation agent, react in a high-pressure sealed state at 100-150°C for 1-4 hours, and indoline can be produced. The highest yield of indoline obtained from the reaction can reach 89.1%. When 2-bromophenethylamine was used as raw material, the yield of indolin...

Claims

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Application Information

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IPC IPC(8): C07D209/04B01J23/72
Inventor 张胜建应丽艳张洪
Owner NINGBO INST OF TECH ZHEJIANG UNIV ZHEJIANG
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