Process for preparing 3-(4-pyridinyl)-2-cyclohene-1-oxime

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

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546156, C07D21353

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active

042464200

ABSTRACT:
An improved method of preparing 3-(4-pyridinyl)-2-cyclohexen-1-one oxime from ethyl 5-oxo-2-[(4-pyridinyl)-carbonyl]hexanoate is a one pot sequence which comprises first heating ethyl 5-oxo-2-[(4-pyridinyl)carbonyl]hexanoate with excess sulfuric acid, neutralizing the excess acid, extracting the resulting 3-(4-pyridinyl)-2-cyclohexen-1-one with isopropyl alcohol, draining off the heavier aqueous layer, adding hydroxylamine hydrochloride to the isopropyl alcohol solution of said 2-cyclohexen-1-one, stirring the mixture at reflux, basifying the mixture and evaporating it to dryness, and isolating 3-(4-pyridinyl)-2-cyclohexen-1-one oxime from the residue. The oxime is an intermediate for preparing 3-(4-pyridinyl)aniline, in turn, an intermediate for preparing rosoxacin, an antibacterial agent.

REFERENCES:
patent: 4026900 (1977-05-01), Gelotte et al.
patent: 4075217 (1978-02-01), Gelotte et al.
patent: 4111946 (1978-09-01), Gelotte et al.

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