1: 54 percent / triethylamine / benzene / 5 h / 0 - 20 °C 2: 88 percent / H2 / Pd/C / dioxane / 24 h / 20 °C / 750.06 Torr 3: 84 percent / H2 / Pd/C / ethanol / 8 h / 20 °C 4: 87 percent / triethylamine / CH2Cl2 / 19 h / 0 - 20 °C 5: 51 percent / TiCl4 / chlorobenzene / 0.28 h / 100 - 110 °C 6: 84 percent / KOH / methanol / 2 h / 20 °C 7: 83 percent / KOH / methanol / 8 h / Heating 8: 85 percent / H2 / Pd/C / methanol / 6 h / 20 °C / 3750.3 Torr 9: 80 percent / Na / liquid ammonia; tetrahydrofuran / 0.75 h / -78 °C View Scheme

ammonia