Abstract Homolytic alkylation of 4-pyridinecarbonitrile with radicals generated by silver nitrate catalyzed oxidative decarboxylation of alkanoic acids and subsequent alkaline hydrolysis afforded 2-alkyl-4-pyridinecarboxylic acids 2a-2e. These were converted into the halogeno-hydroxy substituted anilides 3a-3r via acyl chlorides by reaction with the respective aminophenols at 10 C. Of the compounds tested, 5-chloro-2- ...