1: 1.) pyridine; 2.) H2O / 1.) 100 deg C, 30 min 2: SOCl2, DMF / 0.25 h / Heating 3: pyridine / CHCl3 / Heating 4: 45percent aq. KOH / methanol / 0.5 h 5: 92 percent / K2CO3, N-methylpyrrolidinone / 0.17 h / 140 °C 6: 81 percent / H2 / 5percent Pd/C / ethyl acetate; ethanol / 1 h / Ambient temperature 7: 78 percent / 1,8-bis(dimethylamino)naphthalene / 48 h / 125 °C 8: CF3COOH / CH2Cl2 / Ambient temperature 9: oxalyl chloride / CH2Cl2 / 0.17 h / Heating 10: 46 percent / ethanol; CH2Cl2 / Ambient temperature 11: 1M aq. tetramethylammonium hydroxide / methanol / Ambient temperature View Scheme

1: 92 percent / K2CO3, N-methylpyrrolidinone / 0.17 h / 140 °C 2: 81 percent / H2 / 5percent Pd/C / ethyl acetate; ethanol / 1 h / Ambient temperature 3: 78 percent / 1,8-bis(dimethylamino)naphthalene / 48 h / 125 °C 4: CF3COOH / CH2Cl2 / Ambient temperature 5: oxalyl chloride / CH2Cl2 / 0.17 h / Heating 6: 46 percent / ethanol; CH2Cl2 / Ambient temperature 7: 1M aq. tetramethylammonium hydroxide / methanol / Ambient temperature View Scheme

1: oxalyl chloride / CH2Cl2 / 0.17 h / Heating 2: 46 percent / ethanol; CH2Cl2 / Ambient temperature 3: 1M aq. tetramethylammonium hydroxide / methanol / Ambient temperature View Scheme

1: CF3COOH / CH2Cl2 / Ambient temperature 2: oxalyl chloride / CH2Cl2 / 0.17 h / Heating 3: 46 percent / ethanol; CH2Cl2 / Ambient temperature 4: 1M aq. tetramethylammonium hydroxide / methanol / Ambient temperature View Scheme