quinoline T=150 - 195°C;

1: 93 percent / LiAlH4 / diethyl ether / 22 h / Heating 2: 48 percent aq. HBr, conc. sulfuric acid / 48 h / 25 °C 3: 58 percent / quinoline / 150 - 195 °C View Scheme

1: 70 percent / 85 percent phosphoric acid / 1.42 h / 100 - 170 °C / 20 - 40 Torr 2: 93 percent / LiAlH4 / diethyl ether / 22 h / Heating 3: 48 percent aq. HBr, conc. sulfuric acid / 48 h / 25 °C 4: 58 percent / quinoline / 150 - 195 °C View Scheme

1: 1.) Na, C2H5OH / 1.) 15 min, reflux, 2.) overnight 2: 91 percent / conc. H2SO4, H2O / 24 h / Heating 3: 80 percent / H2SO4 / toluene / 24 h / Heating 4: 70 percent / sodium / toluene / 28 h / Heating 5: 70 percent / 85 percent phosphoric acid / 1.42 h / 100 - 170 °C / 20 - 40 Torr 6: 93 percent / LiAlH4 / diethyl ether / 22 h / Heating 7: 48 percent aq. HBr, conc. sulfuric acid / 48 h / 25 °C 8: 58 percent / quinoline / 150 - 195 °C View Scheme

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

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

aluminum oxide T=200 - 220°C;

1: Na 2: MeOH 3: P2O5 4: LiAlH4 5: Al2O3 / 200 - 220 °C View Scheme

1: P2O5 2: LiAlH4 3: Al2O3 / 200 - 220 °C View Scheme