1: 97 percent / H2 / Raney nickel / methanol / 6 h / 70 °C / 76000.1 Torr 2: 94 percent / LiAlH4 / diethyl ether 3: 77 percent / PBr3 / 10 h / 80 - 90 °C 4: 62 percent / 1) LiNH2 / 1) liq. NH3 - THF, -40 deg C, 2) THF - HMPT, 40 deg C, 3 h 5: 90 percent / H2 / 5percent Pd/BaSO4 - quinoline / methanol / Ambient temperature View Scheme

1: 97 percent / H2 / Raney nickel / methanol / 6 h / 70 °C / 76000.1 Torr 2: 94 percent / LiAlH4 / diethyl ether View Scheme

hydrogen; nickel in methanol T=70°C; P=76000.1 Torr; 6 h;