pyridine hydrochloride in quinoline T=180 - 185°C; 6 h;

sulfuric acid in acetic acid T=95 - 100°C; Yield given;

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 View Scheme

1: With boron tribromide in dichloromethane Cooling; 2: With water T=0°C;

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 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 View Scheme

1: 1.) lithium bis(trimethylsilyl)amide / 1.) THF, 078 deg C, 2 h, 2.) THF, a) -78 deg C, 1 h, b) RT, 20 h 2: H2SO4, glacial acetic acid / 1 h / 95 - 100 °C View Scheme

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