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A kind of preparation method of meta-alkylaniline

A technology of alkylaniline and alkylazobenzene, which is applied in the field of chemistry, can solve the problems of difficulty in obtaining meta-alkylaniline and difficult synthesis, and achieve the effect of less steps and simple preparation method

Inactive Publication Date: 2018-02-06
ANYANG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Its traditional electrophilic substitution of aromatic compounds is difficult to synthesize, such as ①first nitration and reduction, and then introducing an alkyl group to obtain an ortho- or para-alkylaniline; Aniline
Therefore, it is difficult to obtain meta-alkylanilines anyway

Method used

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  • A kind of preparation method of meta-alkylaniline
  • A kind of preparation method of meta-alkylaniline
  • A kind of preparation method of meta-alkylaniline

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] Add 322 mg (1 mmol) of 3,3'-bis(3-pentyl)azobenzene, 224 mg (4 mmol) of iron powder, 0.5 mL of acetic acid, and 20 mL of ethanol into the reaction tube, and stir at room temperature for 24 hours under nitrogen. After the reaction, it was separated by column chromatography to obtain 310 mg of the target product 3-(3-pentyl)aniline with a yield of 95%.

Embodiment 2

[0015] Add 294 mg (1 mmol) of 3,3'-di-tert-butylazobenzene, 224 mg (4 mmol) of iron powder, 0.5 mL of acetic acid, and 20 mL of ethanol into the reaction tube. Stir at room temperature for 24 hours under nitrogen. After the reaction, Separation by column chromatography yielded 280 mg of the target product 3-tert-butylaniline with a yield of 94%.

Embodiment 3

[0017] Add 322 mg (1 mmol) of 3,3'-bis(2-pentyl)azobenzene, 260 mg (4 mmol) of zinc powder, 0.5 mL of hydrochloric acid, and 20 mL of ethanol into the reaction tube, and stir at room temperature for 24 hours under nitrogen. After the reaction, it was separated by column chromatography to obtain 313 mg of the target product 3-(3-pentyl)aniline with a yield of 95%.

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Abstract

A preparation method of m-alkylaniline employs reduction of m-alkylazobenzene to prepare m-alkylaniline, and the reduction may be carried out in two ways; to be specific, in the first way, m-alkylazobenzene, a metal, an acid and a solvent are added directly into a reactor, wherein the metal is iron or zinc, the acid is acetic acid or hydrochloric acid, the solvent is methanol or ethanol, reacting proceeds at room temperature for 24 h, and a product is separated to obtain the m-alkylaniline; in the second way, the reduction is carried out through catalytic hydrogenation to obtain the product m-alkylaniline. The preparation method of the invention is simple and has few steps.

Description

technical field [0001] The invention relates to a preparation method of meta-alkylaniline, which belongs to the field of chemistry. Background technique [0002] Meta-alkylaniline is an important class of basic chemical raw materials, widely used in the synthesis of drugs, pesticides, dyes, materials and natural products. Its traditional electrophilic substitution of aromatic compounds is difficult to synthesize, such as ①first nitration and reduction, and then introducing an alkyl group to obtain an ortho- or para-alkylaniline; Aniline. Therefore it is very difficult to obtain meta-alkylaniline anyway. Contents of the invention [0003] The object of the present invention is to provide a kind of preparation method of meta-alkylaniline. [0004] The preparation method of a m-alkylaniline provided by the present invention, the m-alkylaniline has the structure of formula II, and the m-alkyl azobenzene with the structure of formula I is used to reduce the structure of form...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C209/42C07C211/45C07D309/04
CPCC07C209/42C07D309/04C07C211/45
Inventor 李刚杨素玲吴汉夔何其戈马星星
Owner ANYANG NORMAL UNIV