Triethylamine → N-(4-Chloropyridin-2-yl)pivalamide

Participants

Reaction Steps

Triethylamine (6.8 mL, 48.6 mmol) was added to a stirred solution of 4-chloro-2-aminopyridine, 11, (Townsend, L. B. et al Synthetic Commun. 1997 27, 861-870) (5 g, 38.9 mmol) in dichloromethane (75 mL). After cooling to 0° C. a solution of trimethylacetyl chloride (5.3 mL, 42.8 mmol) in dichloromethane (10 mL) was added dropwise over 15 min. The mixture was allowed to warm to 23° and stirred for 18 h then washed with saturated sodium bicarbonate. The organic layer was dried (Na2SO4) and evaporated in vacuo to give an off-white solid. This was recrystallised from isopropyl ether to afford the title compound as white crystals (5.5 g, 67%). MS(EI) m/e 213, 215 [M+H]+.

Provenance & Evidence