The alkaline hydrolysis of methyl 5-X-picolinates, methyl 4-X-picolinates, and methyl 5-X-nicotinates (X = NO2, Br, H, MeO, or Me2N) in methanol–water (85% w/w) is reported. In each series, the effect of the substituent and ring nitrogen are additive and the rates may be correlated with Hammett σm and σp values.
A. D. Campbell, S. Y. Chooi, L. W. Deady and R. A. Shanks, J. Chem. Soc. B, 1970, 1063 DOI: 10.1039/J29700001063
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