1: hydroxylamine hydrochloride; sodium acetate / pyridine / 17 h / 0 °C 2: 4-(N,N-dimethlyamino)pyridine / acetonitrile / 2 h / 20 °C / Inert atmosphere 3: 2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride / toluene / 3 h / Inert atmosphere; Heating 4: ammonia / methanol / 0 - 20 °C View Scheme

1: 54 percent / ammonia gas / ethanol / 10 h / 100 °C 2: 92 percent / saturated bromine-water / 1 h / Ambient temperature 3: 1.) dibutyltin oxide, 2.) triethylamine / 1.) methanol, 5 h, reflux, 2.) methanol, 1 h, room temperature 4: 88 percent / 40 percent sodium hydrogensulfide aq. / dimethylformamide / 6 h / 60 °C 5: 18 percent / Raney nickel / H2O / 3 h / Heating View Scheme

hydrazine hydrate

ammonia in ethanol T=100°C; 10 h;