Acetic Acid → N,N,4-Trimethylpyridin-2-amine

Participants

Reaction Steps

To a mixture of 2-amino-4-picoline (33 g), NaBH3CN (57 g), formaldehyde (37% aq. solution, 240 mL) in acetonitrile (1 L) and water (200 mL) was added dropwise acetic acid (60 mL) at 0° C. in 2 hr. The resultant solution was stirred at RT for 7 days and then concentrated in vacuo. The residue was basified with solid NaOH to pH 10 and extracted with hexanes (3×700 mL). The combined extract was washed with 1N aq. NaOH and brine, dried over Na2SO4 and evaporated in vacuo to give 2-dimethylamino-4-methylpyridine as a colorless oil (Cmpd 1a, 36 g, 88%). 1H NMR (CDCl3): 2.26 (s, 3H), 3.07 (s, 6H), 6.33 (s, 1H), 6.40 (d, 1H), 8.02 (d, 1H); MS (CI) m/e 137 (MH+).

Provenance & Evidence