Method for preparing 2-amino biphenyl derivative

A technology of aminobiphenyl and aniline derivatives, which is applied in the preparation of amino hydroxyl compounds, organic compounds, amino compounds from amines, etc., can solve the problems of low resource utilization, unfavorable environment, high production cost, etc., and achieve various , Raw materials are easy to obtain, and the ratio of raw materials is reasonable

Active Publication Date: 2014-05-28
WUXI GREEN SEPARATION TECH INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] The above method needs to add a large excess of aniline derivatives and manganese dioxide to obtain the product, and the

Method used

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  • Method for preparing 2-amino biphenyl derivative
  • Method for preparing 2-amino biphenyl derivative
  • Method for preparing 2-amino biphenyl derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Embodiment one: the synthesis of 2-aminobiphenyl

[0041] With aniline and phenylhydrazine as raw materials, the reaction formula is as follows:

[0042]

[0043] (1) Add 0.47 g (5 mmol) of aniline, 0.108 g (1 mmol) of phenylhydrazine, 0.057 g (0.1 mmol) of iron phthalocyanine and 10 ml of methanol into the reaction flask, and react at 20°C;

[0044] (2) TLC tracking reaction until complete completion;

[0045] (3) The crude product obtained after the reaction was separated by column chromatography (petroleum ether: ethyl acetate = 20:1) to obtain the target product (yield 72%).

[0046] 1 H NMR (400 MHz, CDCl 3 ): δ 7.40-7.49 (m, 4H), 7.30-7.38 (m, 1H), 7.10-7.20 (m, 2H), 6.76-6.89 (m, 2H), 4.08 (br, s, 2H); 13 C NMR (75 MHz, CDCl 3 ): δ 143.0, 139.4, 130.5, 129.1, 128.8, 128.5, 128.0, 127.2, 119.0, 115.9.

Embodiment 2

[0047] Example 2: Synthesis of 2-amino-5-fluorobiphenyl

[0048] With 4-fluoroaniline and phenylhydrazine as raw materials, the reaction formula is as follows:

[0049]

[0050] (1) Add 1.11 g (10 mmol) of 4-fluoroaniline, 0.108 g (1 mmol) of phenylhydrazine, 0.057 g (0.1 mmol) of iron phthalocyanine and 10 ml of ethanol to the reaction flask, and react at 70°C;

[0051] (2) TLC followed the reaction until it was completely completed; the crude product obtained after the reaction was separated by column chromatography (petroleum ether: ethyl acetate = 20:1) to obtain the target product (yield 71%).

[0052] 1 H NMR (400 MHz, CDCl 3 ): δ 7.34-7.40 (m, 4H), 7.25-7.33 (m, 1H), 6.78-6.87 (m, 2H), 6.73 (dd, J = 5.6, 9.4 Hz, 1H); 13 C NMR (100 MHz, CDCl 3 ): δ 157.0 (d, J = 237.9 Hz), 138.2, 137.7, 129.0, 128.9, 127.8, 117.6 (d, J = 7.8 Hz), 116.8 (d,J = 22.5 Hz), 114.9 (d, J = 22.3 Hz).

Embodiment 3

[0053] Embodiment three: the synthesis of 2-amino-5-chlorobiphenyl

[0054] With 4-chloroaniline, phenylhydrazine as raw materials, its reaction formula is as follows:

[0055]

[0056] Add 0.89 g (7 mmol) of 4-chloroaniline, 0.108 g (1 mmol) of phenylhydrazine, 0.057 g (0.1 mmol) of iron phthalocyanine (0.1 mmol) and 10 ml of acetonitrile into the reaction flask, and react at 80 ° C; follow the reaction by TLC until it is completely completed; The crude product obtained after the reaction was separated by column chromatography (petroleum ether: ethyl acetate = 20:1) to obtain the target product (yield 69%).

[0057] 1 H NMR (400 MHz, CDCl 3 ): δ 7.40-7.47 (m, 4H), 7.33-7.39 (m, 1H), 7.08-7.14 (m, 2H), 6.74 (d, J = 8.9 Hz, 1H), 4.20 (br, s, 2H); 13 C NMR (75 MHz, CDCl 3 ): δ 141.1, 137.2, 128.9, 127.9, 127.8, 127.1, 126.6, 122.1, 115.6.

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Abstract

The invention discloses a method for preparing a 2-amino biphenyl derivative. The method concretely comprises the following steps: dissolving a polyaniline derivative, a phenylhydrazine derivative and a phthalocyanine metal complex catalyst into a solvent, and reacting at 20-80 DEG C, so as to obtain the 2-amino biphenyl derivative. The polyaniline derivative is used as an initiator, and the prepared 2-amino biphenyl derivative is available in raw material and diverse in variety. The product obtained by using the method disclosed by the invention is diverse in variety, can be directly used, and also can be used for further reaction with the others. Meanwhile, the method is mild in reaction conditions and simple in reaction operation and post-treatment process, the reaction process is catalyzed, the dosage of a reagent and generation and emission of a reaction waste are greatly reduced, and the method is high in productive rate and applicable to large-scale production.

Description

technical field [0001] The invention belongs to the technical field of preparation of organic compounds, and in particular relates to a preparation method of 2-aminobiphenyl derivatives. Background technique [0002] 2-Aminobiphenyl derivatives are a very important class of compounds, which are widely used in medicine, dyes and pesticides. For example, 2-amino-4'-chlorobiphenyl can be used in the synthesis of the fungicide boscalid Boscalid, and 2-amino-3'4'5'-trifluorobiphenyl can be used in the synthesis of the pyrazole amide fungicide Xemium , 2-amino-4-fluoro-3',4'-dichlorobiphenyl can be used in the synthesis of fungicide Bixafen. [0003] There are following methods that can synthesize 2-aminobiphenyl derivatives in the prior art: [0004] A. Wetzel et al. disclose a method for the synthesis of 2-aminobiphenyl derivatives by reacting diazonium salts with aniline derivatives in the presence of titanium trichloride (see: A. Wetzel, V. Ehrhardt, M. R. Heinrich Angew. Ch...

Claims

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Application Information

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IPC IPC(8): C07C209/68C07C211/45C07C211/52C07C213/08C07C215/76C07C217/84C07C211/50
Inventor 邹建平曾润生蒋涛陈胜延
Owner WUXI GREEN SEPARATION TECH INST
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