4-Aminopyridine → 4-(2,2,2-Trimethylacetamido)pyridine

Participants

Reaction Steps

A solution of trimethylacetyl chloride (32.5 mL, 0.264 mol) in dry dichloromethane (50 mL) was added dropwise over 1 h to a stirred suspension of 4-aminopyridine (22.60 g, 0.240 mol) and triethylamine (41.8 mL, 0.300 mol) in dry dichloromethane (360 mL) at 0° C. under nitrogen. The ice bath was removed and the reaction allowed to warm to r.t. overnight. After 17 h, the pale brown mixture was poured into water (500 mL). The organic layer was separated and washed with a dilute aqueous solution of sodium hydrogen carbonate (400 mL). The organic layer was separated, dried over sodium sulfate, filtered and the solvent evaporated in vacuo. The crude solid was recrystallized from ethyl acetate (75 mL)/hexane (50 mL), washed with diethyl ether (2×10 mL) and air dried to yield N-(pyridin-4-yl)pivalamide (29.11 g, 68%) as colourless plate like crystals. 1H NMR: δ (CDCl3, 400 MHz) 1.33 (s, 9H), 7.50 (d, J=6 Hz, 2H), 7.56 (br. s., 1H), 8.49 (d, J=6 Hz, 2H).

Provenance & Evidence