ethanol; sodium 1.) 15 min, reflux, 2.) overnight; Yield given. Multistep reaction;

ammonia

ammonia

1: 91 percent / conc. H2SO4, H2O / 24 h / Heating 2: 80 percent / H2SO4 / toluene / 24 h / Heating 3: 70 percent / sodium / toluene / 28 h / Heating 4: 70 percent / 85 percent phosphoric acid / 1.42 h / 100 - 170 °C / 20 - 40 Torr 5: 93 percent / LiAlH4 / diethyl ether / 22 h / Heating 6: 48 percent aq. HBr, conc. sulfuric acid / 48 h / 25 °C 7: 58 percent / quinoline / 150 - 195 °C View Scheme