Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal
Patent
1977-08-29
1979-01-30
Warren, Charles F.
Chemistry of carbon compounds
Miscellaneous organic carbon compounds
C-metal
424226, C07C10700
Patent
active
041372271
ABSTRACT:
Compounds useful as antibacterial agents are 1-R-1,4-dihydro-4-oxo-7-(BN--N.dbd.N)-3-quinolinecarboxylic acids (I), wherein: (a) BN is dimethylamino where R is methyl, ethyl, n-propyl, n-butyl, n-pentyl or n-octyl; (b) BN is diethylamino where R is n-propyl; or, (c) BN is 4-methyl-1-piperazinyl where R is ethyl. These compounds are prepared by reacting lower-alkyl 7-amino-1-R-1,4-dihydro-4-oxo-3-quinolinecarboxylate (II) with a mineral acid and an alkali nitrite in aqueous medium to produce the corresponding diazonium salt of said 7-aminoquinoline, reacting said diazonium salt with an amine of the formula BNH in the presence of an acid-acceptor to produce lower-alkyl 1-R-1,4-dihydro-4-oxo-7-(BN--N.dbd.N)-3-quinolinecarboxylate and hydrolyzing said 3-quinolinecarboxylate to produce the corresponding 3-carboxylic acid (I). The intermediate lower-alkyl 7-amino-1-R-1,4-dihydro-4-oxo-3-quinolinecarboxylate (II) are prepared in several steps by conventional means starting with m-aniline.
REFERENCES:
patent: 3119808 (1964-01-01), Buckley et al.
Adams et al., J. Chem. Soc., 1949, pp. 3181ff.
Lesher George Y.
Zalay Andrew W.
Bair Robert K.
Sterling Drug Inc.
Warren Charles F.
Wyatt B. Woodrow
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