N-Methylaniline → N-phenyl-N-methyl-2-benzyloxy-5-formylbenzamide

Participants

Reaction Steps

N-Methylaniline (0.18 mL, 1.68 mmol, 2 eq) was added to a solution of 2-benzyloxy-5-formylbenzoic acid (200 mg, 0.84 mmol, 1 eq), 1-hydroxy-7-azabenzotriazole (230 mg, 1.68 mmol, 2 eq), and N-methylmorpholine (0.25 mL, 2.29 mmol, 2.73 eq) in N,N-dimethylformamide (4 mL). To this was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (320 mg, 1.68 mmol, 2 eq) and the reaction mixture stirred overnight. The reaction mixture was diluted with ethyl acetate (20 mL) and washed sequentially with 10% HCl (3×20 mL), brine (20 mL), saturated aqueous sodium bicarbonate (2×20 mL) and brine (20 mL). The organic solution was dried over sodium sulfate and evaporated in vacuo to give a yellow oil (270 mg, 99%). RF (petroleum ether:ethyl acetate 1:1) 0.73. 1H NMR (CDCl3) δ9.79 (s, 1H, O═C—H), 5.01 (s, 2H, CH2Ph), 3.47 (s, 3H, CH3).

Provenance & Evidence