1: H2 / Ra-Ni / methanol; H2O 2: 2) nitric acid / 1) glacial acetic acid, 80 deg C, 1 h, 2) 60 deg C 3: 70 percent / 18percent aq. HCl / Heating 4: 94 percent / chlorobenzene / Heating 5: CH2Cl2 / 2 h / Ambient temperature View Scheme

1: 2) nitric acid / 1) glacial acetic acid, 80 deg C, 1 h, 2) 60 deg C 2: 70 percent / 18percent aq. HCl / Heating 3: 94 percent / chlorobenzene / Heating 4: CH2Cl2 / 2 h / Ambient temperature View Scheme

1: 94 percent / chlorobenzene / Heating 2: CH2Cl2 / 2 h / Ambient temperature View Scheme

triethylamine in dichloromethane Ambient temperature; Yield given;

1: 70 percent / 18percent aq. HCl / Heating 2: 94 percent / chlorobenzene / Heating 3: CH2Cl2 / 2 h / Ambient temperature View Scheme

4: triethylamine / CH2Cl2 / Ambient temperature View Scheme