pyridine in dichloromethane T=20°C;

quinoline; hydrogen; Lindlar's catalyst in hexane P=760 Torr; Ambient temperature; Yield given;

1: 1.) n-butyllithium / 1.) THF, hexane, 1 h, -78 deg C; 2.) 10 min, -78 deg C then to room temp. 2: quinoline, H2 / Lindlar catalyst / hexane; various solvent(s) / 760 Torr / Ambient temperature View Scheme

1: 81 percent / DCC, 4-dimethylaminopyridine / CH2Cl2 / 12 h / Ambient temperature 2: quinoline, H2 / Lindlar catalyst / hexane; various solvent(s) / 760 Torr / Ambient temperature View Scheme

1: 99 percent / Br2 2: 51 percent / KOH / aq. ethanol / 12 h / Heating 3: 81 percent / DCC, 4-dimethylaminopyridine / CH2Cl2 / 12 h / Ambient temperature 4: quinoline, H2 / Lindlar catalyst / hexane; various solvent(s) / 760 Torr / Ambient temperature View Scheme

1: 51 percent / KOH / aq. ethanol / 12 h / Heating 2: 81 percent / DCC, 4-dimethylaminopyridine / CH2Cl2 / 12 h / Ambient temperature 3: quinoline, H2 / Lindlar catalyst / hexane; various solvent(s) / 760 Torr / Ambient temperature View Scheme

1: 100 percent / triphenylphosphine / CH2Cl2 / 3.25 h / 0 °C 2: 1.) n-butyllithium / 1.) THF, hexane, 1 h, -78 deg C; 2.) 10 min, -78 deg C then to room temp. 3: quinoline, H2 / Lindlar catalyst / hexane; various solvent(s) / 760 Torr / Ambient temperature View Scheme

1: 2.3 percent Chromat. / quinoline, H2 / Lindlar catalyst / hexane; various solvent(s) / 760 Torr / Ambient temperature 2: 99 percent / Br2 3: 51 percent / KOH / aq. ethanol / 12 h / Heating 4: 81 percent / DCC, 4-dimethylaminopyridine / CH2Cl2 / 12 h / Ambient temperature 5: quinoline, H2 / Lindlar catalyst / hexane; various solvent(s) / 760 Torr / Ambient temperature View Scheme

1: (COCl)2; dimethylformamide / CH2Cl2 / 1 h / 20 °C 2: 98 percent / pyridine / CH2Cl2 / 20 °C View Scheme