Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science

Mechanisms for the Benzoylation of 2-Aminopyridine

LW Deady and DC Stillman

Australian Journal of Chemistry 32(2) 381 - 386
Published: 1979


Relative rate studies on ring methyl-substituted derivatives of 2-aminopyridine in pyridine solvent show that reaction with benzoyl chloride gives monobenzoyl derivatives by direct reaction on the exocyclic nitrogen (N'). The reaction is analogous to acetylation with acetic anhydride. Reaction in acetone, however, gives, except for the 6-methyl compound, N',N?-dibenzoylamino compounds, even in the presence of excess of amine. The results are shown to be consistent with ring nitrogen benzoylation (N1), followed by rapid N'-benzoylation and intramolecular benzoyl rearrangement from N1 to N'.

© CSIRO 1979

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