aluminium trichloride in dichloromethane 0.5 h; Ambient temperature;

1: 99 percent / N2H4*H2O / Raney-nickel / dioxane; ethanol / 1.) 50 deg C, 1 h; 2.) reflux, 30 min 2: 48 percent / pyridine / 1.) 0 deg C, 1 h; 2.) 20 deg C, 2 h View Scheme

1: 88 percent / KOH / 2 h / 120 °C 2: 83 percent / NaH / 1,2-dimethoxy-ethane / 1 h / 60 °C 3: 100 percent / H2 / 10percent Pd/C / ethyl acetate / 2 h / 2550.2 Torr / Ambient temperature 4: 89 percent / pyridine / CH2Cl2 / 1 h / Ambient temperature 5: 86 percent / NaOH / ethanol; H2O / 2 h / Heating 6: oxalyl chloride, DMF / CH2Cl2 / 1 h / 0 deg C, 30 min, r.t. 30 min 7: 84 percent / AlCl3 / CH2Cl2 / 0.5 h / Ambient temperature View Scheme

1: 83 percent / NaH / 1,2-dimethoxy-ethane / 1 h / 60 °C 2: 100 percent / H2 / 10percent Pd/C / ethyl acetate / 2 h / 2550.2 Torr / Ambient temperature 3: 89 percent / pyridine / CH2Cl2 / 1 h / Ambient temperature 4: 86 percent / NaOH / ethanol; H2O / 2 h / Heating 5: oxalyl chloride, DMF / CH2Cl2 / 1 h / 0 deg C, 30 min, r.t. 30 min 6: 84 percent / AlCl3 / CH2Cl2 / 0.5 h / Ambient temperature View Scheme

1: 88 percent / KOH / 2 h / 120 °C 2: 83 percent / NaH / 1,2-dimethoxy-ethane / 1 h / 60 °C 3: 100 percent / H2 / 10percent Pd/C / ethyl acetate / 2 h / 2550.2 Torr / Ambient temperature 4: 89 percent / pyridine / CH2Cl2 / 1 h / Ambient temperature 5: 86 percent / NaOH / ethanol; H2O / 2 h / Heating 6: oxalyl chloride, DMF / CH2Cl2 / 1 h / 0 deg C, 30 min, r.t. 30 min 7: 84 percent / AlCl3 / CH2Cl2 / 0.5 h / Ambient temperature View Scheme

in pyridine 1.) 0 deg C, 1 h; 2.) 20 deg C, 2 h;

1: 84 percent / 10 N HCl / ethanol / 2 h / Heating 2: 48 percent / pyridine / 1.) 0 deg C, 1 h; 2.) 20 deg C, 2 h View Scheme

1: 2.) Cr2O3 / 1.) AcOH, 25 deg C, 30 min; 2.) AcOH, water, 40 deg C, 2 h 2: 84 percent / 10 N HCl / ethanol / 2 h / Heating 3: 48 percent / pyridine / 1.) 0 deg C, 1 h; 2.) 20 deg C, 2 h View Scheme

1: 89 percent / pyridine / CH2Cl2 / 1 h / Ambient temperature 2: 86 percent / NaOH / ethanol; H2O / 2 h / Heating 3: oxalyl chloride, DMF / CH2Cl2 / 1 h / 0 deg C, 30 min, r.t. 30 min 4: 84 percent / AlCl3 / CH2Cl2 / 0.5 h / Ambient temperature View Scheme

1: oxalyl chloride, DMF / CH2Cl2 / 1 h / 0 deg C, 30 min, r.t. 30 min 2: 84 percent / AlCl3 / CH2Cl2 / 0.5 h / Ambient temperature View Scheme