Alkyl .alpha.-[3-(pyridyl)-anilinomethylene]acetoacetates

Details Alkyl .alpha.-[3-(pyridyl)-anilinomethylene]acetoacetates Alkyl .alpha.-[3-(pyridyl)-anilinomethylene]acetoacetates

1977-09-15

1978-08-15

Trousof, Natalie

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260288CE, 2602955R, 424263, 424266, C07D21342

Patent

active

041071670

ABSTRACT:
Process of reacting 3-PY-aniline (I) with lower-alkyl acetoacetate (II) and tri-(lower-alkyl) orthoformate (III) to produce lower-alkyl .alpha.-(3-PY-anilinomethylene)acetoacetate (IV), heating lower-alkyl .alpha.-(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.

REFERENCES:
chem. Abstracts, 8th Collective Index, p. 5148, -2-[1-(methylamino)ethylidene]-ethyl ester (1966-1975).
Chem. Abstracts, Eck et al., vol. 72, 1972, p. 89719y.

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