Method for preparing imine compound from alcohol and amine through catalytic oxidation

An amine compound, catalytic oxidation technology, applied in the preparation of imino compounds, sulfide preparation, organic chemistry, etc., can solve the problems of long reaction time, low yield of product imine, limited range of reaction substrates, etc. Environmental costs, avoidance of pollution problems, easy and safe operation

Inactive Publication Date: 2017-07-11
ZHEJIANG UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There is also NaOH as a catalyst to catalyze this reaction, but the reaction time is long, the yield of product imine is low, and the reaction can only be carried out under solvent-free conditions, so that the scope of the reaction substrate is limited (European Journal of Organic Chemistry 2012, 4457 )

Method used

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  • Method for preparing imine compound from alcohol and amine through catalytic oxidation
  • Method for preparing imine compound from alcohol and amine through catalytic oxidation
  • Method for preparing imine compound from alcohol and amine through catalytic oxidation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1: N - Preparation of benzylaniline (Formula 1)

[0028] Add 1 mmol of aniline, 1.2 mmol of benzyl alcohol, 0.03 mmol of ABNO, 0.3 mmol of KOH and 0.5 mL of toluene into a 35 mL sealed tube, replace the air in the tube with oxygen, seal the bottle with a rubber stopper, and insert an oxygen balloon , put the reaction bottle into a preheated oil bath and heat to 80°C, and react for 4h. Then directly carry out column chromatography separation, use the mixed solution of ethyl acetate / triethylamine volume ratio 100:1 as the eluent, collect the eluate containing the target compound, and evaporate the solvent to obtain the product N -benzylaniline, the isolated yield is 90%.

Embodiment 2

[0029] Example 2: N - Preparation of benzylaniline (Formula 1)

[0030] Reaction step is with embodiment 1, and difference is that toluene changes mixed xylene into, N - The isolated yield of benzylaniline was 85%.

Embodiment 3

[0031] Example 3: N - Preparation of benzylaniline (Formula 1)

[0032] Reaction step is with embodiment 1, and difference is that toluene changes chlorobenzene into, N - The isolated yield of benzylaniline was 84%.

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Abstract

The invention discloses a method for preparing an imine compound from alcohol and amine through catalytic oxidation. According to the method, an alcohol compound and an amine compound are used as reaction substrates, and a feeding mol ratio of the alcohol compound to the amine compound is 100: 100-60; 9-azabicyclo[3.3.1]nonane N-oxyl free radical is used as a catalyst, potassium hydroxide is used as an auxiliary agent, and a feeding mol ratio of the amine compound to the 9-azabicyclo[3.3.1]nonane N-oxyl free radical to potassium hydroxide is 100: 1-6: 10-50; air is used as an oxidizing agent, the reaction substrates are added into an organic solvent, and the mass of the used organic solvent is 2.5 to 5 times of the reaction substrate the amine compound; and a reaction is carried out at normal pressure at a temperature of 70 to 110 DEG C for 2 to 12 h, and aftertreatment is carried out after completion of the reaction so as to obtain the imine compound. The method provided by the invention is simple and safe to operate, reduces environmental cost due to usage of clean oxygen as the oxidizing agent and prevents the problem of transition-metal pollution by discarding usage of any transition-metal catalyst.

Description

technical field [0001] The invention belongs to the field of compound synthesis, and in particular relates to a method for preparing imine compounds by catalytic oxidation of alcohol and amine as raw materials. Background technique [0002] Imine compounds, also known as Schiff base compounds, are intermediates in the synthesis of pharmaceutical and biologically active compounds as well as fine chemicals. The C=N bonds in imine compounds are also widely used in various organic transformation reactions such as reduction, addition, cyclization, and aziridine. The classic synthesis method of imine compounds is obtained by condensation of amine compounds with aldehydes and ketone compounds, and in many cases, the presence of dehydrating reagents or Lewis acid catalysts is required. [0003] In recent years, the development of new synthetic methods of imine compounds has attracted the attention of a large number of researchers. Among the new methods for the synthesis of various...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C249/02C07C251/24C07C319/20C07C323/45C07D333/22
Inventor 沈振陆李美超宛燕胡信全胡宝祥
Owner ZHEJIANG UNIV OF TECH
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