hydrogen; nickel

quinoline; hydrogen; palladium on barium sulfate in ethyl acetate 2 h; Ambient temperature;

1: 1.) Mg / 1.) THF, 2.) THF, 24 h 2: 81 percent / toluene-4-sulphonic acid / ethanol / 24 h / Heating 3: 1.) KOH, 2.) H2, H2SO4 / 2.) 10percent Pd/C / 1.) ethanol, 1 h, reflux, 2.) ethanol, r.t. 4: 4.31 g / PBr3 / CHCl3 / 4 h / 0 °C 5: 1.) LiNH2, Fe(NO3)3 / 1.) liq. NH3, THF, HMPA, 2.) liq. NH3, THF, HMPA, 40 deg C, 24 h 6: p-TsOH / ethanol / 3 h / Heating 7: 0.1704 g / PBr3 / CHCl3 / 16 h / -30 deg C to r. t. 8: 1.) EtMgBr, CuCl / 1.) THF, 1 h, 2.) THF, 72 h, 35 deg C 9: 50 percent / H2, quinoline / 5 percent Pd-BaSO4 / ethyl acetate / 2 h / Ambient temperature View Scheme

1: 66 percent / conc. HCl, CuCl / toluene / 24 h / 100 °C 2: 84 percent / K2CO3 / benzene / 24 h / Heating 3: 2.) H2 4: 91 percent / BBr3 / CH2Cl2 / 1.) -80 deg C, 3 d, 2.) 72 h 5: 1.) LiNH2, Fe(NO3)3 / 1.) liq. NH3, THF, HMPA, 2.) liq. NH3, THF, HMPA, 40 deg C, 24 h 6: p-TsOH / ethanol / 3 h / Heating 7: 0.1704 g / PBr3 / CHCl3 / 16 h / -30 deg C to r. t. 8: 1.) EtMgBr, CuCl / 1.) THF, 1 h, 2.) THF, 72 h, 35 deg C 9: 50 percent / H2, quinoline / 5 percent Pd-BaSO4 / ethyl acetate / 2 h / Ambient temperature View Scheme

1: 84 percent / K2CO3 / benzene / 24 h / Heating 2: 2.) H2 3: 91 percent / BBr3 / CH2Cl2 / 1.) -80 deg C, 3 d, 2.) 72 h 4: 1.) LiNH2, Fe(NO3)3 / 1.) liq. NH3, THF, HMPA, 2.) liq. NH3, THF, HMPA, 40 deg C, 24 h 5: p-TsOH / ethanol / 3 h / Heating 6: 0.1704 g / PBr3 / CHCl3 / 16 h / -30 deg C to r. t. 7: 1.) EtMgBr, CuCl / 1.) THF, 1 h, 2.) THF, 72 h, 35 deg C 8: 50 percent / H2, quinoline / 5 percent Pd-BaSO4 / ethyl acetate / 2 h / Ambient temperature View Scheme

1: 91 percent / H2, H2SO4 / 10percent Pd/C / ethanol 2: 91 percent / BBr3 / CH2Cl2 / 1.) -80 deg C, 3 d, 2.) 72 h 3: 1.) LiNH2, Fe(NO3)3 / 1.) liq. NH3, THF, HMPA, 2.) liq. NH3, THF, HMPA, 40 deg C, 24 h 4: p-TsOH / ethanol / 3 h / Heating 5: 0.1704 g / PBr3 / CHCl3 / 16 h / -30 deg C to r. t. 6: 1.) EtMgBr, CuCl / 1.) THF, 1 h, 2.) THF, 72 h, 35 deg C 7: 50 percent / H2, quinoline / 5 percent Pd-BaSO4 / ethyl acetate / 2 h / Ambient temperature View Scheme

1: 13.9 g / Li / tetrahydrofuran / 1.) -10 deg C to 0 deg C, 2.) 0 deg C, overnight 2: 100 percent / conc. HCl / methanol / 24 h 3: 91 percent / H2, H2SO4 / 10percent Pd/C / ethanol 4: 91 percent / BBr3 / CH2Cl2 / 1.) -80 deg C, 3 d, 2.) 72 h 5: 1.) LiNH2, Fe(NO3)3 / 1.) liq. NH3, THF, HMPA, 2.) liq. NH3, THF, HMPA, 40 deg C, 24 h 6: p-TsOH / ethanol / 3 h / Heating 7: 0.1704 g / PBr3 / CHCl3 / 16 h / -30 deg C to r. t. 8: 1.) EtMgBr, CuCl / 1.) THF, 1 h, 2.) THF, 72 h, 35 deg C 9: 50 percent / H2, quinoline / 5 percent Pd-BaSO4 / ethyl acetate / 2 h / Ambient temperature View Scheme

1: 98 percent / Li / tetrahydrofuran / 1.) -10 deg C to 0 deg C, 2.) 0 deg C, overnight 2: 62 percent / toluene-4-sulphonic acid / ethanol / 1 h / Heating 3: 91 percent / H2, H2SO4 / 10percent Pd/C / ethanol 4: 91 percent / BBr3 / CH2Cl2 / 1.) -80 deg C, 3 d, 2.) 72 h 5: 1.) LiNH2, Fe(NO3)3 / 1.) liq. NH3, THF, HMPA, 2.) liq. NH3, THF, HMPA, 40 deg C, 24 h 6: p-TsOH / ethanol / 3 h / Heating 7: 0.1704 g / PBr3 / CHCl3 / 16 h / -30 deg C to r. t. 8: 1.) EtMgBr, CuCl / 1.) THF, 1 h, 2.) THF, 72 h, 35 deg C 9: 50 percent / H2, quinoline / 5 percent Pd-BaSO4 / ethyl acetate / 2 h / Ambient temperature View Scheme

1: 100 percent / conc. HCl / methanol / 24 h 2: 91 percent / H2, H2SO4 / 10percent Pd/C / ethanol 3: 91 percent / BBr3 / CH2Cl2 / 1.) -80 deg C, 3 d, 2.) 72 h 4: 1.) LiNH2, Fe(NO3)3 / 1.) liq. NH3, THF, HMPA, 2.) liq. NH3, THF, HMPA, 40 deg C, 24 h 5: p-TsOH / ethanol / 3 h / Heating 6: 0.1704 g / PBr3 / CHCl3 / 16 h / -30 deg C to r. t. 7: 1.) EtMgBr, CuCl / 1.) THF, 1 h, 2.) THF, 72 h, 35 deg C 8: 50 percent / H2, quinoline / 5 percent Pd-BaSO4 / ethyl acetate / 2 h / Ambient temperature View Scheme

1: 62 percent / toluene-4-sulphonic acid / ethanol / 1 h / Heating 2: 91 percent / H2, H2SO4 / 10percent Pd/C / ethanol 3: 91 percent / BBr3 / CH2Cl2 / 1.) -80 deg C, 3 d, 2.) 72 h 4: 1.) LiNH2, Fe(NO3)3 / 1.) liq. NH3, THF, HMPA, 2.) liq. NH3, THF, HMPA, 40 deg C, 24 h 5: p-TsOH / ethanol / 3 h / Heating 6: 0.1704 g / PBr3 / CHCl3 / 16 h / -30 deg C to r. t. 7: 1.) EtMgBr, CuCl / 1.) THF, 1 h, 2.) THF, 72 h, 35 deg C 8: 50 percent / H2, quinoline / 5 percent Pd-BaSO4 / ethyl acetate / 2 h / Ambient temperature View Scheme