4-Chloro-1 -pyridiniopyridinium salts (7) and ( 8) react with primary and secondary arylamines to give high yields of isolable 4-aryliminium salts ( 9) and (1 0). These are readily fragmented into 4-pyridyl(aryl)amines (1 1) and (1 2) in excellent yields on treatment with sodium cyanide or sodium salts of sulphinic acids. The method fails with the more basic aiiphatic amines, since these apparently attack the 2-position of the chloropyridinium ring giving products resulting from ring-opening. Mechanisms of the reactions are discussed.
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