4-Methoxybenzylamine → 6-Chloro-N-(4-methoxy-benzyl)-nicotinamide

Participants

Reaction Steps

A solution of 6-chloronicotinic acid (473 mg, 3 mmol), 4-methoxybenzylamine (412 mg, 3 mmol), 1-(3-dimethlaminopropyl)-3-ethylcarbodiimide hydrochloride (700 mg, 3.6 mmol) and HOBt (200 mg)) in DMF (15 ml) was stirred at room temperature for 3 h. Water (100 ml) was added. The solution was extracted with ethyl acetate (150ml×2), washed with saturated K2CO3 solution (100 ml) and water (200 ml). Organic layer was dried over Na2SO4 and evaporated under reduced pressure to give the desired product (810 mg, 97%). HPLC (6 minute gradient) tR=3.12 min; MS m/z 275.00, 276.95 (M+H]+

Provenance & Evidence