Collect. Czech. Chem. Commun. 1995, 60, 1170-1177

Nucleophilic Substitution in a Series of 4-Nitronicotinic Acid 1-Oxide Derivatives

Radek Pohl, Viktor Prutianov and Svatava Smrčková-Voltrová

Department of Organic Chemistry, Prague Institute of Chemical Technology, 166 28 Prague 6, Czech Republic


Nucleophilic substitution of the nitro group in 4-nitro-3-pyridinecarboxanilide 1-oxide (IIa) afforded 4-hydroxy- (IIb), 4-chloro- (IIc), 4-methoxy- (IId), 4-ethoxy- (IIe), and 4-dimethylamino-3-pyridinecarboxanilide (IIf). The 1H and 13C NMR chemical shifts of the pyridine moiety were correlated with the Hammett constants of the substituent in position 4, with the exception of compound IIb. The reason of this phenomenon is discussed.