Hydrochloric Acid → HCID 88045548, compound

Participants

Reaction Steps

To a stirred vessel containing 2-bromoaniline (10.3 g, 59.9 mmol) was added concentrated hydrochloric acid (15 mL) dropwise while maintaining the mixture temperature <5° C. To the cold suspension was added dropwise a solution of sodium nitrite (4.13 g, 59.9 mmol) in water (12.5 mL). The mixture was stirred and cooled for 15 minutes. A solution of sodium acetate (14.74 g, 180.0 mmol) in water (60 mL) was added dropwise to the reaction mixture. The resulting diazonium salt solution (cloudy yellow suspension) was set aside. While the diazonium salt solution was stirred and cooled, a solution of sodium acetate (4.91 g, 59.9 mmol) in water (17.5 mL) was added to a solution of 2-cyanoacetamide (5.03 g, 59.9 mmol) in water (85 mL) and EtOH (60 mL). The mixture was cooled to a temperature <10° C. at which point the diazonium salt solution was added portion-wise and with vigorous stirring over a span of 25 minutes while maintaining the reaction temperature <10° C. Upon completion of the addition, a thick reddish yellow precipitate formed, which was stirred overnight at room temperature. The solid product was collected by vacuum filtration, washed with water (500 mL), EtOH (500 mL), and Et2O (500 mL), and then dried in a vacuum to afford the title compound as a yellow solid (8.0 g, 53%). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.06-7.13 (m, 1H), 7.43 (t, J=7.71 Hz, 1H), 7.57-7.72 (m, 2H), 7.92-8.02 (m, 2H), 10.03 (s, 1H).

Provenance & Evidence