Sodium Bicarbonate → 2-[(2-Amino-6-bromophenyl)amino]ethanol

Participants

Reaction Steps

To a solution of 2-[(2-bromo-6-nitrophenyl)amino]ethanol (1.95 g, 7.5 mmol) in a mixture of methanol (30 mL) and water (15 mL) sodium acetate trihydrate (56 g) was added. To this mixture titanium trichloride (65 mL, as 15% solution in 10% aqueous HCI) was added drop-wise over period of 20 min. The resulting dark solution was allowed to stir for additional 2 h, and then carefully neutralized with saturated aqueous sodium bicarbonate. The solids were filtered off, and washed with ethyl acetate. The combined organic phase was washed with water and brine, dried over Na2SO4 and concentrated yielding 2-[(2-amino-6-bromophenyl)amino]ethanol as pale-yellow oil (1.61 g, 93%) that was used in the next step without further purification. MS (ESI) m/z: 231.01[M+H].

Provenance & Evidence