pyridine hydrochloride T=170°C; 5.5 h;

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

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

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

1: Li/liq.NH3 / tetrahydrofuran / 0.33 h / -40 °C 2: 68 percent / (COCl)2, DMSO / CH2Cl2 / 0.25 h / -55 °C 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

1: 68 percent / (COCl)2, DMSO / CH2Cl2 / 0.25 h / -55 °C 2: 60 percent / pyridine, K2CO3 / Cu / 17 h / reflux 3: TsOH / benzene / 8 h / reflux 4: Na/liq.NH3 / 3.5 h / -55 - -35 °C 5: 1n HCl / 1 h / reflux 6: 82 percent / pyridine hydrochloride / 5.5 h / 170 °C View Scheme

1: Na/liq.NH3 / 3.5 h / -55 - -35 °C 2: 1n HCl / 1 h / reflux 3: 82 percent / pyridine hydrochloride / 5.5 h / 170 °C View Scheme