Process for preparing flumequine

C - Chemistry – Metallurgy – 07 – D

Patent

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260/271.5, 260/2

C07D 215/18 (2006.01) C07D 215/233 (2006.01) C07D 455/04 (2006.01)

Patent

CA 1159832

Abstract of the Disclosure An improved process for preparing the antimicrobial compound flumequine is disclosed. The first step of the process comprises reacting 4-fluoroaniline with crotonaldehyde under acidic conditions at a temperature between 50 and 60°C. In the second step, the product of the first step is slowly added to a refluxing solvent which forms a binary azeotrope with water and has a boiling point between 90° and 120°C to provide a mixture of 6-fluoroquinaldine and 6-fluorotetrahydroquinaldine. This mixture is then treated with base in the presence of weak acid followed by reducing to provide 6-fluorotetrahydroquinaldine. This compound is then treated according to known procedures to form flumequine.

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