Synthetic method for ortho-alkylaniline

A technology of an alkylaniline and a synthesis method, applied in the field of chemistry, can solve the problems of waste of raw materials, influence on the synthesis efficiency of ortho-position alkylaniline compounds, by-products, etc., and achieves low side reactions, high product yield and easy realization. Effect

Inactive Publication Date: 2018-12-25
ANYANG NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

These two types of synthesis methods are relatively mature and perfect, but in these two types of methods, a large amount of by-products of para-alkylanilines are gener

Method used

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  • Synthetic method for ortho-alkylaniline
  • Synthetic method for ortho-alkylaniline
  • Synthetic method for ortho-alkylaniline

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0013] Example 1:

[0014] Add 294 mg (1 mmol) of 2-heptylazobenzene, 224 mg (4 mmol) of iron powder, 0.5 mL of acetic acid, 20 mL of ethanol, and stirring at room temperature for 24 hours under nitrogen conditions in the reaction tube. After the reaction, column chromatography is used to obtain The target product 2-heptylaniline was 195 mg, and the yield was 95%.

Example Embodiment

[0015] Example 2:

[0016] Add 300 mg (1 mmol) of 2-(3-phenylpropyl)nitrobenzene, 224 mg (4 mmol) of iron powder, 0.5 mL of acetic acid, and 20 mL of ethanol to the reaction tube. Under nitrogen, stir at room temperature for 24 hours. After the reaction, the column Chromatographic separation yielded 202 mg of the target product 2-(3-phenylpropyl)aniline with a yield of 96%.

Example Embodiment

[0017] Example 3:

[0018] Add 254 mg (1 mmol) of 2-(2-ethoxyethyl) azobenzene, 260 mg (4 mmol) of zinc powder, 0.5 mL of hydrochloric acid, and 20 mL of ethanol to the reaction tube, and stir at room temperature for 24 hours under nitrogen. After column chromatography, 155 mg of the target product 2-(2-ethoxyethyl)aniline was obtained with a yield of 94%.

[0019] Add 294 mg (1 mmol) of 2-heptylazobenzene, 33 mg of Pa / C catalyst, 25 mL of methanol, and nitrogen-hydrogen replacement to the reaction kettle. Under 1 MPa pressure, 80 o C was stirred for 10 hours. After the reaction, column chromatography was used to obtain 195 mg of 2-heptylaniline with a yield of 95%.

[0020] The following are the products synthesized by the technical scheme of the present invention and the corresponding yields:

[0021]

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Abstract

The invention relates to a synthetic method for ortho-alkylaniline. The ortho-alkylaniline is obtained by reduction reaction of ortho-alkyl azobenzene. The reduction reaction is carried out to obtainthe ortho-alkylaniline by the following two modes: the first mode comprises: directly adding the ortho-alkyl azobenzene, metal, acid and a solvent in a reaction device, wherein the metal is iron or zinc, the acid is acetic acid or hydrochloric acid, and the solvent is methanol or ethanol; and reacting for 24 hours at a room temperature, and separating the product to obtain the product ortho-alkylaniline; and the second mode comprises: carrying out reduction reaction by catalytic hydrogenation to also obtain the ortho-alkylaniline. The synthetic route is simple, and is easy to implement, side reaction is less, and the yield of products is high.

Description

technical field [0001] The invention relates to a synthesis method of aniline compounds, in particular to a synthesis method of ortho-alkylaniline, and belongs to the field of chemical technology. Background technique [0002] Ortho-alkylanilines are an important class of basic chemical raw materials, widely used in the synthesis of drugs, pesticides, dyes, materials and natural products. There are two traditional synthetic routes: one is the electrophilic Friedel-Crafts alkylation of aromatic rings with aromatic amines and haloalkanes; the other is electrophilic nitration and further reduction of aromatic rings between alkyl aromatic compounds and nitrating reagents. These two types of synthesis methods are relatively mature and perfect, but in these two types of methods, a large amount of by-products of para-alkylanilines are generated, which not only seriously affects the synthesis efficiency of ortho-alkylanilines, but also causes waste of raw materials , a large number...

Claims

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Application Information

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IPC IPC(8): C07C209/42C07C211/47C07C211/45C07C213/02C07C217/76
CPCC07C209/42C07C213/02C07C211/47C07C211/45C07C217/76
Inventor 李刚杨素玲张丽萍赵建英陈晓婷
Owner ANYANG NORMAL UNIV
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