hydrazine hydrate; nickel in ethanol T=45°C; 0.5 h;

1: 87 percent / H2 / 5percent Pd/C / acetic acid; HClO4 / 24 h / 30 °C / 2280 Torr 2: 67 percent / 25percent HCl / 1.) methanol, 90 deg C, 6 h; 2.) r.t., 17 h View Scheme

1: 82 percent / NaOAc / ethyl acetate; H2O / 4 h / Ambient temperature 2: 87 percent / H2 / 5percent Pd/C / acetic acid; HClO4 / 24 h / 30 °C / 2280 Torr 3: 67 percent / 25percent HCl / 1.) methanol, 90 deg C, 6 h; 2.) r.t., 17 h View Scheme

1: 97 percent / NaBH4, SiO2 / CHCl3; propan-2-ol / 0.25 h 2: 40percent hydrazine hydrate / Raney Ni / ethanol / 0.5 h / 45 °C View Scheme

hydrogenchloride 1.) methanol, 90 deg C, 6 h; 2.) r.t., 17 h;