1: hydrogen; palladium 10 on activated carbon / tetrahydrofuran / 2 h / 20 °C / 750.08 Torr 2: thionyl chloride / dichloromethane / 2 h / |Reflux 3: pyridine / dichloromethane / 18 h / 20 °C 4: methylhydrazine / dichloromethane / 2 h / -10 °C 5: 1,2-dichloro-ethane; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 24 h / 20 °C 6: hydrogen; palladium 10 on activated carbon / tetrahydrofuran / 4 h / 20 °C / 750.08 Torr View Scheme