Hydrochloric Acid → HCID 89825272, compound

Participants

Reaction Steps

To a stirred vessel containing 2-bromo-5-fluoroaniline (20.0 g, 105 mmol) was added concentrated hydrochloric acid (26 mL, 3.0 eq) dropwise while maintaining the mixture temperature <5° C. To the cooled suspension was added dropwise a solution of sodium nitrite (7.1 g, 103 mmol) in water (25 mL). The mixture was stirred and cooled for 15 minutes. A solution of sodium acetate (26.0 g, 317 mmol) in water (120 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 (8.6 g, 105 mmol) in water (30 mL) was added to a solution of 2-cyanoacetamide (8.8 g, 105 mmol) in water (150 mL) and EtOH (120 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 addition of the diazonium salt solution, a thick reddish yellow precipitate formed, and the mixture was stirred overnight at room temperature. The solid product was collected by vacuum filtration, washed with water (300 mL) and EtOH (800 mL), and dried in a vacuum to afford the title compound as a red solid (20.0 g, 66.9%). 1H NMR (400 MHz, DMSO-d6) δ ppm 14.52 (1H, s), 8.31 (1H, s), 8.12 (1H, s), 7.73-7.70 (1H, m), 7.36-7.33 (1H, m), 7.00-6.95 (1H, m).

Provenance & Evidence