Dimethylformamide → N-(2-naphtyl)methyl 3-(2-aminophenyl)-2-methyl-2-propenamide

Participants

Reaction Steps

Into 4 ml of dimethylformamide, 0.65 g (2.2 mmol) of (E) 3-(2-aminophenyl)-2-methyl-2-propenoic acid p-nitrophenyl ester and 0.69 g (4.4 mmol) of 2-naphtylamine (manufactured by Aldrich Chemical Co., Inc.) were dissolved; and, with 0.36 ml of triethylamine (manufactured by Wako Pure Chemical Industries, Ltd.) being added thereto, the mixture was reacted at room temperature for 20 hours. After the completion of the reaction was verified by TLC, ethyl acetate and water were added to the mixture. The resulting ethyl acetate layer was fractionated, and was washed several times with a 5% aqueous sodium hydrogencarbonate solution and then with a saturated aqueous sodium chloride solution. After the washed solution was dried with magnesium sulfate anhydride, the solvent was evaporated under a reduced pressure, whereby a crude product was obtained. This product was refined by a silica gel column chromatography (developing solvent: methylene chloride/methanol=95/5), whereby 1.39 g of the aimed compound were obtained (yield: quantitative).

Provenance & Evidence