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The quinaldyl ketone, 4‐phenyl‐3‐(quinolin‐2‐yl)‐butan‐2‐one was prepared by two methods: (a) benzylation of 1‐(1H‐quinolin‐2‐ylidene)propan‐2‐one in the presence of sodium hydride in dimethylformamide and (b) by the benzylative demethoxycarbonylation of methyl 2‐(1H‐quinolin‐2‐ylidene)‐3‐oxobutanoate in the presence of lithium bromide in hexamethylphosphoramide at 135°. In the absence of acid, the compound exists exclusively in the tautomeric form, 4‐phenyl‐3‐(1H‐quinolin‐2‐ylidene)butan‐2‐one.

Tautomerism in Quinaldyl Ketones.-Reaction of benzyl bromide with the quinoline (I) or the β-keto ester (IV) gives the quinaldyl ketone (III). In the presence of acid, ( III) is in equilibrium with its tautomer (V). -(DOUGLASS, J. E.; MICHELENA, E.; ATAEI, A.; DOTSON, D. L.; LO, H.-H.; J.

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