The cyano-group in 1-alkyl-4-cyanopyridinium salts is readily replaced by hydrazine or aliphatic amines. The carbamoyl group does not have similar reactivity. Halogen exchange occurs during the quaternisation of 2-chloro-4-cyanopyridine with methyl iodide.
J. K. Landquist, J. Chem. Soc., Perkin Trans. 1, 1976, 454 DOI: 10.1039/P19760000454
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