Acetanilides are converted into 2-chloroquinoline-3-carbaldehydes in good yield by the action of Vilsmeier's reagent in phosphoryl chloride solution. The reaction is shown to involve successive conversion of the acetanilide into an imidoyl chloride and then an N-(or-chloroviny1)aniline. The latter enamine is diformylated at its P-position and subsequently cyclised to the chloroquinolinecarbaldehyde. The diformylated intermediates may be isolated in several cases and separately cyclised with polyphosphoric acid. * n.d. = not determined.

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The 2-chloro-groups of the title compounds have been replaced by H, I, OH, SR, Li, C02H, CHO, Ph, piperidine, and N, (giving a tetrazole). The aldehyde group has also been converted into oxime, hydrazone, and acrylic acid derivatives. From these and related derivatives a variety of fused quinolines have been made including thieno-, pyridazino-, tropono-, pyrano-, thiopyrano-, and furo-quinolines.

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