Benzylamine → HCID 15296706, compound

Participants

Reaction Steps

To a room temperature solution of 7-methoxy-1-(1-methylethoxy)-2-naphthalenecarboxylic acid (200 mg, 0.77 mmol) in 5 mL of THF is added N,N-carbonyldiimidazole (162 mg, 1.00 mmol). The solution is heated at reflux for 1 hour and cooled slightly. Benzylamine (0.50 mn) is added and the reaction mixture is stirred at room temperature overnight. The mixture is diluted with ethyl acetate and washed with brine. The organic layer is dried over MgSO4, filtered, and concentrated in vacuo. The crude product is chromatographed on silica gel eluting with hexane:ethyl acetate (2:1) to provide 7-methoxy-1-(1-methylethoxy)-N-(phenylmethyl)-2-naphthalene-carboxamide in 73% yield; mp 88°-90° C.

Provenance & Evidence