hydrogen; palladium on activated charcoal in methanol; water T=25°C; P=760 Torr; 3 h;

palladium in isopropyl alcohol

1.1: 2 h / 50 °C 1.2: NaH / dimethylformamide / 2.5 h / 80 °C 1.3: 48 percent / HCl / H2O / 3 h / 0 - 5 °C / pH 7.2 2.1: 69 percent / H2 / Pd/C / methanol; H2O / 3 h / 25 °C / 760 Torr View Scheme

1.1: KOH / methanol; H2O / 6 h / 25 °C 2.1: (COCl)2 / benzene / 19 h / 25 °C 3.1: 58.5 g / NH3 / CH2Cl2 / 1.58 h / 5 - 15 °C 4.1: 2 h / 50 °C 4.2: NaH / dimethylformamide / 2.5 h / 80 °C 4.3: 48 percent / HCl / H2O / 3 h / 0 - 5 °C / pH 7.2 5.1: 69 percent / H2 / Pd/C / methanol; H2O / 3 h / 25 °C / 760 Torr View Scheme

1.1: 58.5 g / NH3 / CH2Cl2 / 1.58 h / 5 - 15 °C 2.1: 2 h / 50 °C 2.2: NaH / dimethylformamide / 2.5 h / 80 °C 2.3: 48 percent / HCl / H2O / 3 h / 0 - 5 °C / pH 7.2 3.1: 69 percent / H2 / Pd/C / methanol; H2O / 3 h / 25 °C / 760 Torr View Scheme