Ammonium Hydroxide → HCID 9795138, compound

Participants

Reaction Steps

To a room temperature solution of 7-methoxy-1-(1-methylethoxy)-2-naphthalenecarboxylic acid (141 mg, 0.54 mmol) in 10 mL of THF is added N,N-carbonyldiimidazole (105 mg, 0.65 mmol). The solution is heated at reflux for 1 hour and cooled slightly. Aqueous NH4OH (2.5 mL) is added and the reaction mixture is stirred at room temperature for 40 minutes then partitioned between 1:1 hexane:ethyl acetate and brine. The organic layer is dried over MgSO4, filtered, and concentrated in vacuo. The crude product is recrystallized from hexane and ethyl acetate to provide 7-methoxy-1-(1 methylethoxy)-2-naphthalenecarboxamide in 68% yield; mp 172°-174° C.

Provenance & Evidence