1: 1.) NaH / 1.) CH3CN, 0 deg C, 40 min, 2.) CH3CN, 3 h 2: 99 percent / 1percent methanol. NaOH / 1 h / Ambient temperature 3: 99 percent / H2 / 5percent Pd/C / methanol / 2 h / Ambient temperature 4: pyridine / 0.5 h / 0 °C 5: pyridine / 2.5 h / Ambient temperature 6: sat. aq. NH4OH / 1 h / 0 - 20 °C View Scheme

hydrogen; palladium on activated charcoal in methanol P=1471.02 Torr; 3 h;