palladium on activated charcoal; hydrazine hydrate in methanol; water 0.5 h; Heating;

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 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 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 View Scheme

1: 87 percent / AcOH, n-BuNH2 / methanol / 18 h / 22 °C 2: 64 percent / AcCl, FeCl3 / CH2Cl2 / 1 h / 0 - 5 °C 3: hydrazine hydrate, 10percent Pd-C / methanol; H2O / 0.5 h / Heating View Scheme

1: aq. NaOH / methanol / 0.5 h / Heating 2: 80 percent / pyridine / CH2Cl2 / 5 - 10 °C 3: H2O / 2 h / Heating View Scheme

1: sodium hydroxide; water / |Large scale 2: pyridine / |Large scale 3: hydrogenchloride / water / |Large scale View Scheme

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

sodium hydroxide in methanol 0.5 h; Heating; Yield given;