- Process for preparing antibacterial compounds
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4-(4-Halo-3-nitrophenyl)pyridines, useful as intermediates in the synthesis of antibacterial 1-alkyl-1,4-dihydro-4-oxo-7-pyridinyl-3-quinolinecarboxylic acids, are obtained by nitrating 4-(4-halophenyl)pyridines. The 4-(4-halo-3-nitrohenyl)pyridines may be converted to the antibacterial agents by reducing them to 4-(3-aminophenyl)pyridines and then subjecting the amino compounds to suitable known reactions.
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- Alkyl α-[3-(pyridyl)-anilinomethylene]acetoacetates
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Process of reacting 3-PY-aniline (I) with lower-alkyl acetoacetate (II) and tri-(lower-alkyl) orthoformate (III) to produce lower-alkyl α-(3-PY-anilinomethylene)acetoacetate (IV), heating lower-alkyl α-(3-PY-anilinomethylene)acetoacetate (IV), to produce 3-acetyl-1,4-dihydro-4-oxo-7-PY-quinoline (V) which is tautomeric with 3-acetyl-4-hydroxy-7-PY-quinoline (VA), reacting V (or VA) with a lower-alkylating agent to produce 3-acetyl-1-(lower-alkyl)-1,4-dihydro-4-oxo-7-PY-quinoline (VI) and converting VI to 1-(lower-alkyl)-1,4-dihydro-4-oxo-7-PY-3-quinolinecarboxylic acid (VII), where PY is 4(or 3)-pyridyl or 4(or 3)-pyridyl having one or two lower-alkyl substituents. The compounds of formula VII are known antibacterial agents.
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- Cyclic alkylidenyl N-(lower-alkyl)-3-(pyridinyl)anilinomethylenemalonates
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Cyclic alkylidenyl N-(lower-alkyl)-3-PY-anilinomethylenemalonates (I), where PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents, are prepared by reacting cyclic alkylidenyl (lower-alkoxy)methylenemalonate (II) with N-(lower-alkyl)-3-PY-aniline (III). Also, I is heated with polyphosphoric acid to produce 1-(lower-alkyl)-1,4-dihydro-4-oxo-7-PY-3-quinolinecarboxylic acid, known antibacterial agents. The N-(lower-alkyl)-3-PY-anilines are produced by reducing the corresponding N-(3-PY-phenyl)-(lower-alkanamides).
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