Isatoic Anhydride → 2-Amino-N-(prop-2-yn-1-yl)benzamide

Participants

Reaction Conditions

Reaction Steps

A solution of propargylamine (1.00 mL, 14.6 mmol) in DMF (4.0 mL) was added dropwise to a solution of isatoic anhydride (1.57 g, 9.72 mmol) in DMF (8.0 mL) at 45° C. The solution was stirred at 45° C. for 16 h and diluted with water and CH2Cl2. The aqueous phase was extracted with CH2Cl2 washed with water, brine, dried and concentrated. The crude product was recrystallised from EtOAc/petrol to give 2-amino-N-propargylbenzamide (0.85 g, 51%) as a colourless solid; mp 100-101° C., lit. [29] 98-100° C.; δH (400 MHz, DMSO-d6) 3.08 (t, J=2.4 Hz, 1H, C≡CH), 3.97 (dd, J=5.6, 2.4 Hz, 2H, CH2), 6.45 (s, 2H, NH2), 6.49 (t, J4,5=J5,6=7.8 Hz, 1H, H5), 6.68 (d, J3,4=7.8 Hz, 1H, H3), 7.13 (t, J3,4=J4,5=7.8 Hz, 1H, H4), 7.46 (d, J5,6=7.8 Hz, 1H, H6), 6.61 (t, J=5.6 Hz, 1H, NH).

Provenance & Evidence