Ammonia → N-tert-Butyl-3-methylpyridine-2-carboxamide

Participants

Reaction Conditions

Reaction Steps

A suspension of 2-cyano-3-methyl pyridine (400 g; 3.4 mol) in 800 mL of t-butanol was heated at 70° C. Concentrated sulfuric acid (400 mL) was added over 45 min. The reaction was complete after a further 30 min. at 75° C. The reaction mixture was diluted with water (400 mL) and toluene (600 mL) and brought to pH 10 with concentrated aqueous ammonia. The temperature was kept at 50°-55° C. during work-up. The toluene phase was separated, the aqueous layer extracted again with toluene and the combined toluene phases were washed with water. Removal of the toluene yielded 633 g (97%) of crystalline N-(1,1-dimethylethyl)-3-methyl-2-pyridinecarboxamide: m.p. 56°-58° C.; NMR 9200 MHz, CDCl3)δ1.52 (s,9H); 2.75 (s,3H); 7.25 (dd,1H, J=7.5, 5 Hz); 7.58 (dd,1H, J=7.5, 1.2 Hz); 8.08 (br s, 1H); 8.40 (dd,1H, J=5), 1.2 Hz); mass spectrum, m/e (rel intensity) 192M+ (12), 177 (49). Anal. Calcd for C11H16N2O: C,68.68; H, 8.13; N,14.40. Found: C,68.71; H,8.39; N,14.57.

Provenance & Evidence