pyridine in dichloromethane T=5 - 10°C; 4 h;

1: 80 percent / MeONa / methanol / 1 h / 0 °C 2: 53 percent / AcCl, FeCl3 / CH2Cl2 / 3 h / 0 - 5 °C 3: 95 percent / aq. NaH2PO2 / 10percent Pd-C / ethyl acetate / 0.58 h / Heating 4: 89 percent / ethanol; H2O / 24 h / Heating 5: 70 percent / aq. HCl / 2.5 h / Heating 6: 87 percent / pyridine / CH2Cl2 / 4 h / 5 - 10 °C View Scheme

1: 95 percent / aq. NaH2PO2 / 10percent Pd-C / ethyl acetate / 0.58 h / Heating 2: 89 percent / ethanol; H2O / 24 h / Heating 3: 70 percent / aq. HCl / 2.5 h / Heating 4: 87 percent / pyridine / CH2Cl2 / 4 h / 5 - 10 °C View Scheme

1: aq. NaOH / methanol / 0.5 h / Heating 2: 87 percent / pyridine / CH2Cl2 / 4 h / 5 - 10 °C View Scheme

1: hydrazine hydrate, 10percent Pd-C / methanol; H2O / 0.5 h / Heating 2: aq. NaOH / methanol / 0.5 h / Heating 3: 87 percent / pyridine / CH2Cl2 / 4 h / 5 - 10 °C View Scheme

1: 100 percent / ZnCl2 / CH2Cl2 / 1 h / Heating 2: 1.) hexamethylenetetramine, 2.) aq. AcOH / 1.) ethanol, reflux, 90 min, 2.) ethanol, reflux 3: 87 percent / AcOH, n-BuNH2 / methanol / 18 h / 22 °C 4: 64 percent / AcCl, FeCl3 / CH2Cl2 / 1 h / 0 - 5 °C 5: hydrazine hydrate, 10percent Pd-C / methanol; H2O / 0.5 h / Heating 6: aq. NaOH / methanol / 0.5 h / Heating 7: 87 percent / pyridine / CH2Cl2 / 4 h / 5 - 10 °C View Scheme

1: 81 percent / MeONa / methanol / 4 h / -10 - -5 °C 2: 42 percent / FeCl3 / CH2Cl2 / 5 h / 20 °C 3: 85 percent / 10percent Pd-C, aq. NaH2PO2 / ethyl acetate / 0.58 h / Heating 4: 70 percent / aq. HCl / 2.5 h / Heating 5: 87 percent / pyridine / CH2Cl2 / 4 h / 5 - 10 °C View Scheme

1: 89 percent / ethanol; H2O / 24 h / Heating 2: 70 percent / aq. HCl / 2.5 h / Heating 3: 87 percent / pyridine / CH2Cl2 / 4 h / 5 - 10 °C View Scheme

1: 70 percent / aq. HCl / 2.5 h / Heating 2: 87 percent / pyridine / CH2Cl2 / 4 h / 5 - 10 °C View Scheme

1: 1.) hexamethylenetetramine, 2.) aq. AcOH / 1.) ethanol, reflux, 90 min, 2.) ethanol, reflux 2: 87 percent / AcOH, n-BuNH2 / methanol / 18 h / 22 °C 3: 64 percent / AcCl, FeCl3 / CH2Cl2 / 1 h / 0 - 5 °C 4: hydrazine hydrate, 10percent Pd-C / methanol; H2O / 0.5 h / Heating 5: aq. NaOH / methanol / 0.5 h / Heating 6: 87 percent / pyridine / CH2Cl2 / 4 h / 5 - 10 °C View Scheme