quinoline; hydrogen; Lindlar's catalyst in hexane P=2070.2 Torr;

1: 92 percent / H2, quinoline / Lindlar's catalyst / hexane / 2070.2 Torr 2: 70 percent / PBr3, pyridine / diethyl ether / 1.) overnight, 2.) reflux, 2 h View Scheme

1: 52 percent / LAH / diethyl ether / 1a) overnight, 1b) reflux, 6 h 2: 74 percent / PBr3, pyridine / diethyl ether / 1a) overnight, 2) reflux, 2 h 3: 1) sodium / 1) benzene, DMF, 2) benzene, reflux, 12 h 4: 58 percent / NaCl / H2O; dimethylsulfoxide / 8 h / 180 °C View Scheme

1: 92 percent / H2, quinoline / Lindlar's catalyst / hexane / Ambient temperature 2: 81 percent / triethylamine / CH2Cl2 / 0.5 h / -5 °C 3: 1.) Mg, iodine, 2.) HMPA / 1.) THF, 40-50 deg C, 1.5 h, 2.) 0-10 deg C, 30 min, 3.) RT, overnight View Scheme

1: 52 percent / LAH / diethyl ether / 1a) overnight, 1b) reflux, 6 h 2: 74 percent / PBr3, pyridine / diethyl ether / 1a) overnight, 2) reflux, 2 h 3: 1) sodium / 1) benzene, DMF, 2) benzene, reflux, 12 h 4: 58 percent / NaCl / H2O; dimethylsulfoxide / 8 h / 180 °C 5: 54 percent / lithium aluminium monoethoxy hydride / diethyl ether 6: 60 percent / pyridine / 48 h View Scheme

1: 52 percent / LAH / diethyl ether / 1a) overnight, 1b) reflux, 6 h 2: 74 percent / PBr3, pyridine / diethyl ether / 1a) overnight, 2) reflux, 2 h 3: 1) sodium / 1) benzene, DMF, 2) benzene, reflux, 12 h 4: 58 percent / NaCl / H2O; dimethylsulfoxide / 8 h / 180 °C 5: 54 percent / lithium aluminium monoethoxy hydride / diethyl ether View Scheme

Multi-step reaction with 2 steps 1: 1a.) ethylmagnesium bromide, 1b.) cuprous chloride / 1a.) THF, reflux, 6 h, 1b.) 0 deg C, 15 min, 3.) reflux, 9 h2: 66 percent / p-TsOH / methanol / 4 h / Heating