2,4-Dimethoxybenzaldehyde → N-(2,4-dimethoxybenzyl)prop-2-yn-1-amine

Participants

Reaction Steps

To a solution of 2,4-dimethoxybenzaldehyde (2.5 g, 15.06 mmol) in methanol (100 ml) was added prop-2-yn-1-amine (1.0 g, 18.18 mmol) at room temperature. The reaction mixture was stirred at room temperature for 1.5 hours, and then cooled to 0° C. NaBH4 (1.0 g, 26.32 mmol) was then added in portions over 15 minutes. The mixture was warmed up and stirred at room temperature for an additional 2 hours. The reaction was quenched with brine (200 mL), and partitioned between brine and ethyl acetate. The organic phase was washed with brine, dried over MgSO4, filtered and concentrated to afford the title compound which was used in next step without further purification. 1H NMR (400 MHz, dimethylsulfoxide-d6): δ 2.07 (br s, 1H), 3.04 (s, 1H), 3.27 (s, 2H), 3.63 (s, 2H), 3.74 (s, 3H), 3.76 (s, 3H), 6.46 (d, J=8.0 Hz, 1H), 6.52 (s, 1H), 7.15 (d, J=8.4 Hz, 1H).

Provenance & Evidence