Polychloroaromatic compounds. Part IV. Oxidation of 2- and 4-N-alkylaminotetrachloropyridines and nucleophilic substitution of tetrachloronitropyridines

Abstract

The reaction of pentachloropyridine and its 1-oxide with various primary amines is described. The resulting 2- and 4-N-alkylamino-derivatives are oxidised with peroxytrifluoroacetic acid to give nitroso-, nitro-, and amino-compounds for which a mechanism is suggested. The 2- and the 4-nitrotetrachloropyridine are found to suffer nucleophilic displacement of the nitro-group. The synthetic use of these nitro-compounds for producing inaccessible 2- or 4-substituted tetrachloropyridines such as the 4-morpholino-compound is discussed.