Phosphorus oxychloride → 2-Chloro-3-quinolinecarboxaldehyde

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Where the starting material above is a 2-chloro-3-cyanoquinoline, this can be prepared by starting from an appropriate substituted acetanilide. This is heated with phosphoryl chloride and dimethylformamide to give the corresponding 2-chloro-3-quinolinecarboxaldehyde. The process involved is discussed in detail by meth-Cohn et al., J. Chem. Soc., Perkin Trans. 1, 1981, 1520. The chloroquinolinecarboxaldehyde is then reacted with hydroxylamine hydrochloride, formic acid and sodium formate with heating to give the corresponding 3-cyano-2(1H)-quinolinone. This is then heated with an excess of phosphoryl chloride to give the desired 2-chloro-3-cyanoquinoline.

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