pyridine; thionyl chloride in benzene Heating;

1: 80 percent / pyridine / benzene / 2.5 h / Heating 2: 1.) potassium / 1.) toluene, 90 deg C, 2.) reflux, 15 h 3: NaOH / ethanol; H2O / 1 h / Heating 4: 1.) H2 / 1.) 10percent Pd/C / 1.) ethanol, 2.) overnight 5: 90 percent / LiAlH4 / tetrahydrofuran / Ambient temperature 6: 92 percent / thionyl chloride, pyridine / benzene / Heating View Scheme

1: 1.) potassium / 1.) toluene, 90 deg C, 2.) reflux, 15 h 2: NaOH / ethanol; H2O / 1 h / Heating 3: 1.) H2 / 1.) 10percent Pd/C / 1.) ethanol, 2.) overnight 4: 90 percent / LiAlH4 / tetrahydrofuran / Ambient temperature 5: 92 percent / thionyl chloride, pyridine / benzene / Heating View Scheme

1: 1.) H2 / 1.) 10percent Pd/C / 1.) ethanol, 2.) overnight 2: 90 percent / LiAlH4 / tetrahydrofuran / Ambient temperature 3: 92 percent / thionyl chloride, pyridine / benzene / Heating View Scheme

1: NaOH / ethanol; H2O / 1 h / Heating 2: 1.) H2 / 1.) 10percent Pd/C / 1.) ethanol, 2.) overnight 3: 90 percent / LiAlH4 / tetrahydrofuran / Ambient temperature 4: 92 percent / thionyl chloride, pyridine / benzene / Heating View Scheme

1: 38 percent / NaH / toluene / 48 h / Heating 2: 90 percent / LiAlH4 / tetrahydrofuran / Ambient temperature 3: 92 percent / thionyl chloride, pyridine / benzene / Heating View Scheme

1: 90 percent / LiAlH4 / tetrahydrofuran / Ambient temperature 2: 92 percent / thionyl chloride, pyridine / benzene / Heating View Scheme

chlorine in dichloromethane T=10 - 20°C; 0.25 h; Yield given. Title compound not separated from byproducts;