Method for synthesizing 1-alkyl-2-alkoxyl-3-indole aldoxime derivant

A technology of indole aldoxime and alkoxy is applied in the field of synthesizing new compounds of 1-alkyl-2-methoxy-3-indole aldoxime, which can solve the problems of slow reaction speed, long production cycle and the like, Achieve the effect of low cost, low environmental burden and simple operation

Inactive Publication Date: 2011-07-20
BOHAI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But the reaction speed is slow and the production cycle is long

Method used

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  • Method for synthesizing 1-alkyl-2-alkoxyl-3-indole aldoxime derivant
  • Method for synthesizing 1-alkyl-2-alkoxyl-3-indole aldoxime derivant
  • Method for synthesizing 1-alkyl-2-alkoxyl-3-indole aldoxime derivant

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Take indolinone as substrate to obtain 1-alkyl-2-chloro-3-indole aldehyde through Vilsmeier-Hacck formylation reaction and alkylation reaction, in the presence of potassium hydroxide and fatty alcohol, the described Fatty alcohol can be reacted with methanol or ethanol or propanol or butanol or pentanol or cyclohexanol at 50-80°C, and the reaction temperature should be kept at 70°C or under reflux; the reaction time is 1-3 hours. Layer chromatography TLC monitoring, after the reaction is complete, directly add hydroxylamine hydrochloride to the mixture without any treatment (that is, the intermediate product obtained in the alkoxylation reaction can directly add hydroxylamine hydrochloride to carry out the next reaction) and the oximation reaction can occur. The temperature is constant, the reaction time is 1-2 hours, and the ratio of the 1-alkyl-2-chloro-3-indolaldehyde, hydroxylamine hydrochloride, potassium hydroxide, fatty alcohol and water is 1mmol: 2mmol: 2mmol: 5-...

Embodiment 2

[0035] POCl 3 (17.5 mL) was added drop by drop to dimethylformamide DMF (17.5 mL) under vigorous stirring in an ice bath. Then 2-indolinone (10g, 75.2mol) was dissolved in 100mL CHCl 3 , then slowly dropwise added to POCl 3 and DMF mixture, vigorously stirred for half an hour. Stirring was then stopped and left overnight. The next day, after 8 hours of reflux under vigorous stirring, the CHCl was distilled off with a rotary evaporator. 3 , and then add 200 mL of water to it. After standing overnight, the precipitate was filtered and recrystallized with ethanol to obtain 5.5 g of orange-red needle-like crystals, namely 2-chloro-3-indolaldehyde, with a yield of 40.8%.

[0036] With the above product and K 2 CO 3 Dissolve in an appropriate amount of acetone at a molar ratio of 1:1.5 (add a small amount of potassium iodide to the reaction solution when the alkylating agent is ethyl bromide and benzyl chloride), and then put it into a round-bottomed flask equipped with a sti...

Embodiment 3

[0039] With 1-ethyl-2-chloro-3-indole aldehyde as raw material reaction, other reaction conditions and methods are the same as in Example 1, to obtain 1-ethyl-2-methoxyl group-3-indole aldoxime, yield It is 67.7%, and its melting point is 102.0-103.0°C.

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Abstract

The present invention relates to a method used for synthesizing derivatives of 1-alkyl-2-alkoxy-3-indole aldehyde oxime. Indole-one is used as basic material and treated through Vilsmeier-Hacck formylation reaction and alkylation reaction to prepare 1-alkyl-2-chlorine-3-indole aldehyde; under the conditions with potassium hydroxide and fatty alcohol and at the temperature of 50 to 80 DEG C, the reaction is monitored by a thin chromatogram TLC; after the reaction is completed, no treatment is required and hydroxylamine hydrochloride is directly added into the mixture for oximation reaction; the reaction temperature is maintained; the reaction lasts for 1 to 2 hours; the ratio of the 1-alkyl-2-chlorine-3-indole aldehyde, the hydroxylamine hydrochloride, the potassium hydroxide, the fatty alcohol and water is equal to 1mmol to 2mmol to 2mmol to from 5ml to 8 ml to 1ml; finally water is added for sedimentation, and the novel compounds of the category of the 1-alkyl-2-chlorine-3-indole aldehyde can be separated through filtration and chromatography. The method has the advantages of mild reaction conditions, process under atmospheric pressure, simple operation, less investment in the equipment, low production costs, less pollution and high yield.

Description

technical field [0001] The invention relates to a method for synthesizing 1-alkyl-2-methoxy (ethoxy)-3-indole aldoxime novel compounds by using indolone as a raw material. Background technique [0002] Oxime compounds are a class of compounds with very good biological activity. They have excellent biological activities such as insecticidal, acaricidal, bactericidal, herbicidal, detoxifying, and synergistic, and many products also have the advantages of low toxicity and low residue. It is not only widely used in medicine, but also an important class of bioactive compounds in pesticides. From the first oxime ester pesticide cottonocarb developed in 1963 to methomyl and aldicarb, which are still used today, oxime pesticides have developed to a certain extent, and a large number of fungicides and herbicides have been developed. With the rapid development of modern science and technology and the advancement of drug synthesis methods, a large number of oxime compounds with novel ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/34
Inventor 高文涛高德朋郭惠常明琴汤立军孙曙光
Owner BOHAI UNIV
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