1: toluene, reflux, 1 h 2: 25 percent / Raney-Ni / methanol / 23 h / reflux 3: 60 percent / pyridine, K2CO3 / Cu / 17 h / reflux 4: TsOH / benzene / 8 h / reflux 5: Na/liq.NH3 / 3.5 h / -55 - -35 °C 6: 1n HCl / 1 h / reflux 7: 82 percent / pyridine hydrochloride / 5.5 h / 170 °C View Scheme