hydroxylamine hydrochloride in ethanol 11.5 h; Ambient temperature;

hydrogenchloride; hydroxylamine hydrochloride Yield given. Multistep reaction;

1: 1.) NBS; 2.) triethylamine / 1.) DMF, -20 deg C, 1 h, 0 deg C, 30 min; 2.) DMF, Et2O, RT, 18 h 2: 80 percent / boric acid, H2 / Raney Ni (W-2) / ethanol; H2O / 12 h / 760 Torr / Ambient temperature View Scheme

N-bromosuccinmide; triethylamine in water; N,N-dimethyl-formamide T=20°C; 18 h;

1: N-chlorosuccinimide, pyridine / CHCl3 / 0.17 h 2: Et3N / CHCl3 / 0.5 h / Ambient temperature View Scheme