3'-Aminoacetophenone → HCID 52984174, compound

Participants

Reaction Steps

To a stirred solution of 3-amino acetophenone (1.0 g, 7.35 mmol) in dimethylformamide (DMF) (10.0 mL) was added triethylamine (Et3N) (1.11 g, 11.03 mmol) at 0° C. followed by the slow addition of 2-bromopropionyl bromide (1.75 g, 8.08 mmol). The reaction was stirred at room temperature (rt) under N2 atmosphere for 3 h, diluted with water (50.0 mL) and the precipitated pale brown solid was filtered and dried to give the title product in 80% yield. 1H NMR (CDCl3, 400 MHz): 8.47 (br s, NH), 8.09-8.08 (m, 1H), 7.92 (dd, J=8.0 Hz, J=1.2 Hz, 1H), 7.73 (dd, J=8.0 Hz, J=1.2 Hz, 1H), 7.46 (t, J=8.0 Hz, 1H), 4.60 (q, J=6.8 Hz, 1H), 2.62 (s, 3H), 1.96 (d, J=7.2 Hz, 3H). 13C NMR (CDCl3, 100 MHz): 198.0, 167.8, 137.8, 137.7, 129.5, 124.8, 124.6, 119.5, 44.8, 26.7, 22.7. ESI-MS calcd for C11H12BrNO2 (M+Na)+291.99. found 292.0.

Provenance & Evidence