1: 97 percent / potassium hydride, 1,3-diaminopropane / 18 h / Ambient temperature 2: 93 percent / imidazole, / dimethylformamide / 2 h / Ambient temperature 3: 93 percent / Et3N, CuI / (Ph3P)2PdCl2 / 4 h / 50 °C 4: 93 percent / H2 / 5percent Pd-C / ethanol; ethyl acetate / 4 h View Scheme

pyridine in dichloromethane T=0 - 20°C;

pyridine 1) -5 deg C, 0.5 h, 2) 0 deg C, 6 h;

1: 93 percent / pyridine / 1) -5 deg C, 0.5 h, 2) 0 deg C, 6 h 2: 85 percent / LiBr / acetone / 6 h / Heating 3: 1) Li / 1) (C2H5)2O, -10 deg C, 2 h, 0-5 deg C, 1 h, 2) room temperature, 14 h 4: 95 percent / Na, liq. NH3 / diethyl ether / 15 h / -35 °C View Scheme

1: 93 percent / pyridine / 1) -5 deg C, 0.5 h, 2) 0 deg C, 6 h 2: 85 percent / LiBr / acetone / 6 h / Heating 3: 1) Li / 1) (C2H5)2O, -10 deg C, 2 h, 0-5 deg C, 1 h, 2) room temperature, 14 h 4: 95 percent / Na, liq. NH3 / diethyl ether / 15 h / -35 °C 5: 96 percent / pyridine / 24 h / Ambient temperature View Scheme

1: 95 percent / H2, quinoline / Pd-CaCO3 / hexane / Ambient temperature 2: 1.) MeSO2Cl, Et3N, 2.) LiBr / 1.) CH2Cl2, r.t., 3 h, 2.) acetone, r.t., 5 h 3: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 30 min, 2.) THF, r.t., 2 h 4: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 30 min, 2.) THF, r.t., 2 h 5: 73 percent / silica gel / tetrahydrofuran; H2O / 5 h / 25 °C 6: 22 percent / hydrazine hydrate, KOH / bis-(2-hydroxy-ethyl) ether / 3 h / Heating 7: 92 percent / 5percent aq. HCl / tetrahydrofuran / 1 h / Ambient temperature 8: 86 percent / pyridine / 5 h / 0 °C View Scheme

quinoline; hydrogen; Lindlar's catalyst in various solvent(s) T=20°C; P=760.051 Torr; 2 h;

sodium tetrahydroborate; RuCl3*xH2O in water; dimethylammonium 2,4-dichlorophenoxyacetate T=0°C; 1 h;

1: sodium hydride; ethylenediamine / mineral oil / 3.5 h / 40 - 65 °C 2: Jone's reagent / water; acetone / 18 h / 0 - 25 °C View Scheme

1: Lindlar-catalyst; methanol / Hydrogenation 2: acetic acid / 170 °C View Scheme