sodium hydroxide; hydrogen; palladium on activated charcoal in ethanol P=760 Torr; 2 h; Ambient temperature;

quinoline; hydrogen; Lindlar's catalyst in ethanol 0.5 h; Ambient temperature;

quinoline; hydrogen; Lindlar's catalyst in ethanol P=760 Torr; 0.266667 h; Ambient temperature;

1: 7.8 percent / LiCl, LiHCO3 / dimethylformamide / 0.5 h / Heating 2: 72 percent / H2, 0.1 N NaOH / 5percent Pd/C / ethanol / 2 h / 760 Torr / Ambient temperature View Scheme

1: 98 percent / H2 / 5percent Pd/C / toluene; ethyl acetate / 2 h / 760 Torr / Ambient temperature 2: 95 percent / pyridinium chlorochromate adsorbed on alumina / CH2Cl2 / 12 h 3: 64 percent / tri-N-methylanilinium perbromide / tetrahydrofuran / 1) 15 min, 0 deg C, 2) 15 min, rt 4: 90 percent / LiHCO3, LiBr / dimethylformamide / 0.5 h / Heating 5: 60 percent / H2, quinoline / 5percent Pd/CaCO3 / ethanol / 0.27 h / 760 Torr / Ambient temperature 6: 72 percent / H2, 0.1 N NaOH / 5percent Pd/C / ethanol / 2 h / 760 Torr / Ambient temperature View Scheme

1: 95 percent / pyridinium chlorochromate adsorbed on alumina / CH2Cl2 / 12 h 2: 64 percent / tri-N-methylanilinium perbromide / tetrahydrofuran / 1) 15 min, 0 deg C, 2) 15 min, rt 3: 90 percent / LiHCO3, LiBr / dimethylformamide / 0.5 h / Heating 4: 60 percent / H2, quinoline / 5percent Pd/CaCO3 / ethanol / 0.27 h / 760 Torr / Ambient temperature 5: 72 percent / H2, 0.1 N NaOH / 5percent Pd/C / ethanol / 2 h / 760 Torr / Ambient temperature View Scheme

1: 64 percent / tri-N-methylanilinium perbromide / tetrahydrofuran / 1) 15 min, 0 deg C, 2) 15 min, rt 2: 90 percent / LiHCO3, LiBr / dimethylformamide / 0.5 h / Heating 3: 60 percent / H2, quinoline / 5percent Pd/CaCO3 / ethanol / 0.27 h / 760 Torr / Ambient temperature 4: 72 percent / H2, 0.1 N NaOH / 5percent Pd/C / ethanol / 2 h / 760 Torr / Ambient temperature View Scheme

1: 90 percent / LiHCO3, LiBr / dimethylformamide / 0.5 h / Heating 2: 60 percent / H2, quinoline / 5percent Pd/CaCO3 / ethanol / 0.27 h / 760 Torr / Ambient temperature 3: 72 percent / H2, 0.1 N NaOH / 5percent Pd/C / ethanol / 2 h / 760 Torr / Ambient temperature View Scheme

piperidine; hydrogen; Lindlar's catalyst in ethyl acetate 2 h; Ambient temperature;