Abstract: | A convenient method for the synthesis of 2-chloro-5-hydroxynicotinonitrile ( 10 ) via 5-amino-2-chloro-3-methylpyridine ( 3 ) is described. Subsequent conversions provided the basic metabolite 2 of (S)-2-(3-t-butylamino-2-hydroxypropoxy)-3-cyanopyridine ( 1 ). 13C Nmr data is also presented to characterize 2-chloro-5-fluoro-3-methylpyridine ( 5 ), a by-product in the Schiemann reaction having unexpected 1H and 19F nmr spectra. |