hydrogen; palladium on activated charcoal in 1,4-dioxane P=2068.6 Torr; 8 h;

1: 1.) lithium bis(trimethylsilyl)amide / 1.) a.) THF, -78 deg C, b.) -10 deg C, 2 h, 2.) a.) from -78 deg C to 25 deg C, 3-4 h, b.) RT, 4 h 2: 1.) Mg, CCl4 / 1.) ethanol, 50 to 55 deg C, 5 to 6 h, 2.) benzene, reflux, 8 h 3: 58 percent / pyridine hydrochloride / quinoline / 6 h / 180 - 185 °C 4: 91 percent / H2 / 5percent Pd/C / dioxane / 8 h / 2068.6 Torr View Scheme

1: 1.) Mg, CCl4 / 1.) ethanol, 50 to 55 deg C, 5 to 6 h, 2.) benzene, reflux, 8 h 2: 58 percent / pyridine hydrochloride / quinoline / 6 h / 180 - 185 °C 3: 91 percent / H2 / 5percent Pd/C / dioxane / 8 h / 2068.6 Torr View Scheme

1: 58 percent / pyridine hydrochloride / quinoline / 6 h / 180 - 185 °C 2: 91 percent / H2 / 5percent Pd/C / dioxane / 8 h / 2068.6 Torr View Scheme

1: 1.) Mg, CCl4 / 1.) ethanol, 50 to 55 deg C, 5 to 6 h, 2.) benzene, reflux, 8 h 2: 58 percent / pyridine hydrochloride / quinoline / 6 h / 180 - 185 °C 3: 91 percent / H2 / 5percent Pd/C / dioxane / 8 h / 2068.6 Torr View Scheme