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Synthesis of 2-aminobiphenyl compounds

A synthetic method, the technology of aminobiphenyl, applied in the direction of amino compound preparation, organic compound preparation, chemical instruments and methods, etc., can solve the problems of high price, high industrialization cost, high equipment requirements, etc., and achieve low production cost and easy operation , the effect of high reaction yield

Inactive Publication Date: 2009-02-18
ZHEJIANG UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This method requires the use of sodium amide reagent, which is expensive, and requires very strict anhydrous and anaerobic operating conditions, high requirements for equipment, and high industrialization costs

Method used

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  • Synthesis of 2-aminobiphenyl compounds
  • Synthesis of 2-aminobiphenyl compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] The synthesis of embodiment 1 2-biphenylcarboxylic acid

[0036] Add 50g of 9-fluorenone and 400mL of diphenyl ether into a 1L three-necked flask equipped with mechanical stirring, reflux condenser and thermometer, stir and dissolve, add 130g of potassium hydroxide at the same time, heat and reflux for 6 hours, and the reaction is complete. Cool down, acidify with 36-37% hydrochloric acid to pH=1-2, filter with suction, and dry to obtain 2-biphenylcarboxylic acid, the content is ≥99% by HPLC analysis, and the yield is 98%.

Embodiment 2

[0037] The synthesis of embodiment 2 2-biphenylformic acid

[0038] Add 50g of 9-fluorenone and 400mL of toluene into a 1L three-necked flask equipped with mechanical stirring, reflux condenser and thermometer, stir to dissolve, add 130g of potassium hydroxide at the same time, heat and reflux for 6 hours, and the reaction ends. Cool down, acidify with 36-37% hydrochloric acid to pH=1-2, filter with suction, and dry to obtain 2-biphenylcarboxylic acid, the content is ≥99% by HPLC analysis, and the yield is 98%.

Embodiment 3

[0039]Synthesis of Example 3 2-biphenylcarboxylic acid

[0040] Add 10g of 9-fluorenone and 80mL of diphenyl ether into a 1L three-necked flask equipped with mechanical stirring, reflux condenser and thermometer, stir to dissolve, add 20g of potassium tert-butoxide at the same time, heat and reflux for 8 hours, and the reaction is completed. Cool down, acidify with 36-37% hydrochloric acid to pH = 1-2, filter with suction, and dry to obtain 2-biphenylcarboxylic acid, the content is ≥99% by HPLC analysis, and the yield is 85%.

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Abstract

The present invention relates to a synthesis method of 2-phenylaniline compounds as shown in the formula (V). The synthesis method comprises the following steps: substituted 9-fluorenone as shown in the formula (I) reacts under alkaline conditions to prepare a compound (II); the compound (II) and acylation agent perform acyl halogenation reaction to prepare a compound (III); the compound (III) performs ammoniation reaction to prepare a compound (IV); and the compound (IV) performs Hofmann degradation reaction to prepare the compound (V). The present invention discloses a novel synthesis method of the 2-phenylaniline compounds, and the present invention has the advantages of mild reaction conditions, easy operation, high utilization rate of atoms, high reaction yield, low production cost, suitability for industrial production, high implementation value and the socioeconomic benefits.

Description

(1) Technical field [0001] The invention relates to a method for synthesizing a pharmaceutical intermediate 2-aminobiphenyl compound. (2) Background technology [0002] 2-Aminobiphenyl compounds are important intermediates, which are widely used in many fields such as medicine, pesticide and chemical industry. There are not many reports on the synthesis methods of these compounds. GB 597809 reports the preparation of 2-aminobiphenyl by nitration and reduction with biphenyl as a raw material. This method generates 4-nitrobiphenyl and 2-nitrobiphenyl simultaneously during the nitration reaction. The separation of the two is difficult, and the recovery The rate is low, not suitable for industrialized production. Shen Yongcun etc. have reported the synthesis process of 2-phenylbenzamide (the new synthesis process of 2-phenylbenzamide, "Fine Chemical Industry", 1999, 2, 59.), the Haller- Preparation of 2-phenylbenzamide by the Bauer method. This method requires the use of sod...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/44C07C211/52C07C209/50
Inventor 张兴贤
Owner ZHEJIANG UNIV OF TECH
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