A method for the synthesis of a bifenasine intermediate

By employing diazotization, coupling, halogenation, and amination reactions, the problems of high equipment requirements, high energy consumption, and significant safety hazards in the existing methods for preparing 4-methoxy-3-aminobiphenyl have been solved, achieving a low-cost, high-yield, and green synthesis.

CN117623947BActive Publication Date: 2026-05-12SHAOXING SHANGYU XINYINBANG BIOCHEMICAL CO LTD
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Patent Information

Application Number
CN202311626140.5
Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
Filing Date
2023-11-30
Publication Date
2026-05-12
Estimated Expiration
2043-11-30

AI Technical Summary

Technical Problem

Existing methods for preparing 4-methoxy-3-aminobiphenyl have problems such as high requirements for production equipment, high energy consumption, high cost, significant safety hazards, and difficulty in separating by-products.

Method used

Using 4-methoxyaniline as the starting material, 4-methoxybenzene diazonium salt is generated through diazotization, followed by coupling with benzene, and then halogenation and amination reactions. This avoids dangerous reactions such as high-temperature alkaline fusion, nitration, and high-pressure catalytic hydrogenation reduction. The substitution reaction is carried out using halogenation reagents and metal amines, which reduces the requirements for equipment and safety hazards.

Benefits of technology

This method successfully reduced production costs, avoided safety hazards from dangerous reactions, improved reaction selectivity and product purity, and provided a green, environmentally friendly, and high-yield synthetic method.

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Abstract

The application discloses a synthesis method of bifenzhydrylamine intermediate, and relates to the technical field of organic synthesis. The synthesis method comprises the following steps: taking 4-methoxy aniline as a starting material, and obtaining 4-methoxy benzene diazonium salt through a diazotization reaction; decomposing the 4-methoxy benzene diazonium salt to form an aryl free radical, adding a certain amount of benzene to carry out a coupling reaction, and obtaining 4-methoxy biphenyl; then carrying out halogenation reaction on the 4-methoxy biphenyl through a halogenating reagent to obtain 4-methoxy-3-halogen biphenyl; finally, adding a metal amide to carry out nucleophilic substitution, and obtaining 4-methoxy-3-amino biphenyl. The synthesis method of 4-methoxy-3-amino biphenyl provided by the application avoids relatively dangerous and harsh reactions such as nitration reaction and Grignard reaction, the reaction process is relatively safe, raw materials are cheap and easy to obtain, the reaction yield is high, the reaction condition is mild, the synthesis route is short, the equipment investment is small, and the method is easy to industrialize.
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