C(=O)CCCC(=[O:7])C.[N:9]1C=CC(C2CCCC(=O)C=2)=[CH:11][CH:10]=1.C1(=O)CCCC=C1.O=C(C)CC[CH:33]([C:39]([C:41]1[CH:46]=[CH:45][N:44]=CC=1)=O)[C:34](OCC)=O.S(=O)(=O)(O)O.[CH:53](O)([CH3:55])[CH3:54]>>[N:9]1[CH:10]=[CH:11][C:55]([C:41]2[CH2:39][CH2:33][CH2:34][C:45](=[N:44][OH:7])[CH:46]=2)=[CH:53][CH:54]=1This invention resides in an improvement in the process for preparing 3-(4-pyridinyl)-2-cyclohexen-1-oxime by heating ethyl 5-oxo-2-[(4-pyridinyl)carbonyl]hexanoate under aqueous acidic conditions to produce 1-(4-pyridinyl)-hexan-1,5-dione, reacting said hexan-1,5-dione with a basic condensing agent to produce said 3-(4-pyridinyl)-2-cyclohexen-1-one, and converting said cyclohexen-1-one to its oxime, said improvement being a one pot sequence consisting of first heating ethyl 5-oxo-2-[(4-pyridinyl)carbonyl]hexanoate with excess aqueous sulfuric acid, neutralizing the excess acid, shaking the resulting mixture well with isopropyl alcohol to extract the 3-(4-pyridinyl)-2-cyclohexen-1-one, draining off the heavier warm (40° to 50° C.) aqueous layer, adding hydroxylamine hydrochloride to the isopropyl alcohol solution of 3-(4-pyridinyl)-2-cyclohexen-1-one, stirring the mixture at reflux, basifying the mixture and evaporating it to dryness, and isolating the 3-(4-pyridinyl)-2-cyclohexen-1-one oxime from the residue. In a preferred embodiment three mole-equivalents of sulfuric acid were used per mole of ethyl 5-oxo-2-[(4-pyridinyl)carbonyl]hexanoate, the excess sulfuric acid was neutralized with aqueous sodium hydroxide solution and the reaction mixture was basified after oxime formation with concentrated ammonium hydroxide.
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