Process for 6,7-dihydro-9-fluoro-5-methyl-1-oxo-1H,5H-benzo(ij)q

Details Process for 6,7-dihydro-9-fluoro-5-methyl-1-oxo-1H,5H-benzo(ij)q Process for 6,7-dihydro-9-fluoro-5-methyl-1-oxo-1H,5H-benzo(ij)q

1980-02-19

1981-11-17

Daus, Donald G.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

546153, 546180, C07D45504, C07D21522, C07D21518

Patent

active

043012884

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.

REFERENCES:
patent: 3896131 (1975-07-01), Gerster
Elderfield, et al., J. Am. Chem. Soc., vol. 71, pp. 1906-1911 (1949).
Mirek, Chemical Abstracts, 62, 5252b (1965).
Palmer, The Structure and Reactions of Heterocyclic Compounds, Edwin Arnold, Ltd., London, (1967), pp. 110-111.
Jones, et al., J. Chem. Soc. Trans., 97, pp. 632-644 (1910).

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