1: potassium carbonate / dimethylformamide 2: acetic acide / Heating 3: pyridine View Scheme

1: acetic acide / Heating 2: pyridine View Scheme

pyridine

1: 1.) thionyl chloride / 1.) 100 deg C, 30 min; 2.) 70 deg C, 100 deg C, 15 min 2: 70 percent / trimethylbenzyl ammonium hydroxide / 16 h / 70 °C 3: 80 percent / hydrogen / Raney nickel / ethanol / 60 °C View Scheme

1: 1.) thionyl chloride / 1.) 100 deg C, 30 min; 2.) 70 deg C, 100 deg C, 15 min 2: 70 percent / trimethylbenzyl ammonium hydroxide / 16 h / 70 °C 3: 80 percent / hydrogen / Raney nickel / ethanol / 60 °C 4: 70 percent / CH2Cl2 / 1 h View Scheme

1: 1.) thionyl chloride / 1.) 100 deg C, 30 min; 2.) 70 deg C, 100 deg C, 15 min 2: 70 percent / trimethylbenzyl ammonium hydroxide / 16 h / 70 °C 3: 80 percent / hydrogen / Raney nickel / ethanol / 60 °C 4: 70 percent / CH2Cl2 / 1 h 5: ethanol / 20 h / Heating View Scheme

1: 1.) thionyl chloride / 1.) 100 deg C, 30 min; 2.) 70 deg C, 100 deg C, 15 min 2: 70 percent / trimethylbenzyl ammonium hydroxide / 16 h / 70 °C 3: 80 percent / hydrogen / Raney nickel / ethanol / 60 °C 4: 70 percent / CH2Cl2 / 1 h 5: ethanol / 24 h / Heating View Scheme

1: 1.) thionyl chloride / 1.) 100 deg C, 30 min; 2.) 70 deg C, 100 deg C, 15 min 2: 70 percent / trimethylbenzyl ammonium hydroxide / 16 h / 70 °C 3: 80 percent / hydrogen / Raney nickel / ethanol / 60 °C 4: 70 percent / CH2Cl2 / 1 h 5: 69 percent / ethanol / 24 h / Heating View Scheme