hydrogen; palladium on activated charcoal in methanol 20 h;

hydrazine hydrate in ethanol 18 h; Heating;

1: 100 percent / LiAlH4 / diethyl ether / 0.25 h / 60 °C 2: 95 percent / H2 / Pd/C / methanol / 20 °C / atmospheric pressure View Scheme

1: 100 percent / LiAlH4 / diethyl ether / 0.25 h / 60 °C 2: 95 percent / H2 / Pd/C / methanol / 20 °C / atmospheric pressure 3: 17 percent / K2CO3; CuO; pyridine / 6 h / Heating 4: 36 percent / H2 / Pd/C / ethyl acetate / 20 °C / atmospheric pressure 5: 11 mg / BBr3 / CH2Cl2 / 1.5 h / 20 °C View Scheme

sodium hydroxide T=20°C; 8 h;

1: 19.5 g / hydrazine dihydrate / ethanol / 12 h / Heating 2: pyridine / 1.) 0 deg C, 15 min, 2.) 20 deg C, 2 h 3: 7.1 g / sodium carbonate / ethane-1,2-diol / 0.05 h / Heating View Scheme

1: 19.5 g / hydrazine dihydrate / ethanol / 12 h / Heating 2: pyridine / 1.) 0 deg C, 15 min, 2.) 20 deg C, 2 h View Scheme