4-Bromoaniline → 1-((4-Bromophenyl)diazenyl)pyrrolidine

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-bromoaniline (1.7 g, 9.88 mmol) in conc. HCl (2 mL) was added a solution of NaNO2 (682 mg, 9.88 mmol) in water (3 mL) at 0° C. The solution was stirred at 0° C. for 10 minutes, followed by the addition of pyrrolidine (844 mg, 11.86 mmol) in KOH solution (1 mL, 1 N). The resultant mixture was stirred at 0° C. for 0.5 h. The formed precipitate was collected by filtration, washed with 1 mL of ethanol and dried to give the title compound as a yellow solid (1.5 g, yield 60%). MS (ES+) C10H12BrN3 requires: 253, 255, found 254, 256 [M+H]+, purity: 93%.

Provenance & Evidence