Charles M. Leir - Saint Paul MN Kirk G. Hedberg - Saint Paul MN Joel R. Jacobson - Saint Paul MN
Assignee:
Minnesota Mining and Manufacturing Company - St. Paul MN
International Classification:
C07D45504 C07D21522 C07D21518
US Classification:
546 94
Abstract:
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. degree. and 60. degree. 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. degree. and 120. degree. 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.
Process For 6,7-Dihydro-9-Fluoro-5-Methyl-1-Oxo-1H,5H-Benzo(Ij)Quinolizine-2-Carboxy Lic Acid
Charles M. Leir - New Richmond WI Kirk G. Hedberg - Minneapolis MN
Assignee:
Minnesota Mining and Manufacturing Company - St. Paul MN
International Classification:
C07D45504 C07D21522
US Classification:
546 94
Abstract:
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. degree. and 60. degree. C. In the second step, the product of the first step is treated 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.