ammonium hydroxide; hydrogen; nickel in ethanol Ambient temperature;

nickel monoaluminide in ethanol

1: 93 percent / potassium iodide / dimethylsulfoxide / 5 h / 120 °C 2: 81 percent / 28percent ammonia water, H2 / Raney nickel / ethanol / Ambient temperature View Scheme

1: 2.) concd. H2SO4 / 1.) RT, 3 h, 2.) 150 deg C, 1 h 2: 93 percent / potassium iodide / dimethylsulfoxide / 5 h / 120 °C 3: 81 percent / 28percent ammonia water, H2 / Raney nickel / ethanol / Ambient temperature View Scheme

1: 42 percent / thionyl chloride / CHCl3 / 2.5 h / Heating 2: dimethylformamide / 5 h / Heating 3: hydrazine monohydrate / ethanol / 4 h / Heating View Scheme

1: lithium aluminum hydride / diethyl ether / 1 h / Ambient temperature 2: 67 percent / diethyl azodicarboxylate, triphenylphosphine / tetrahydrofuran / 20 h / Ambient temperature 3: 13.2 g / 85percent hydrazine monohydrate / ethanol / 1.5 h / Heating View Scheme