Hydrogen Bromide → HCID 6610498, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 2,4-dimethyl-6-nitroaniline (5 g, 30.12 mmol) in water (38 mL) was added HBr (15 mL, 40%). The mixture was heated to reflux for 10 minutes and then cooled to 0° C. A solution of NaNO2 (2.07 g) in water (12 mL) was added dropwise with cooling. The mixture was stirred for 30 minutes and then added slowly to a stirred mixture of CuBr (4.33 g) in HBr (12 mL) and water (23 mL) at RT. The reaction mixture was stirred at RT for 30 minutes, heated to reflux for 3 hours, and then steam distilled. The distillate was extracted with DCM (3×30 mL), washed with aqueous saturated NaHCO3 and saturated NaCl, and concentrated to give the title compound as a solid (1.8 g, 26%). 1H NMR (400 MHz, CDCl3) δ ppm 7.26 (1H, s), 7.17 (1H, s), 2.39 (3H, s), 2.27 (3H, s).

Provenance & Evidence