hydrogenchloride in pyridine; methanol T=190°C; 0.666667 h;

1: 97 percent / benzene / Heating 2: 76 percent / dioxane / 25 h / Heating 3: 92.8 percent / hydrogen / 10 percent palladium/charcoal / ethanol; H2O / 110 h / Ambient temperature 4: 54 percent / hydrogenchloride / ethanol / 2.5 h / Heating 5: 22.4 percent / 10 percent palladium/carbon / decahydronaphthalene / 6 h / 205 °C 6: 71 percent / hydrogen chloride / methanol; pyridine / 0.67 h / 190 °C View Scheme

1: 76 percent / dioxane / 25 h / Heating 2: 92.8 percent / hydrogen / 10 percent palladium/charcoal / ethanol; H2O / 110 h / Ambient temperature 3: 54 percent / hydrogenchloride / ethanol / 2.5 h / Heating 4: 22.4 percent / 10 percent palladium/carbon / decahydronaphthalene / 6 h / 205 °C 5: 71 percent / hydrogen chloride / methanol; pyridine / 0.67 h / 190 °C View Scheme

1: benzene / Heating 2: 71 percent / dioxane / 1.) 100 min, 2.) reflux, 22 h 3: hydrogen / 10 percent palladium/charcoal / ethanol; H2O / Ambient temperature 4: 32 percent / conc. hydrochloric acid / ethanol; H2O / 2.5 h / Heating 5: 60 percent / 6 N hydrochloric acid / 7.5 h / Heating 6: 27 percent / 10 percent palladium/charcoal / various solvent(s) / 50 h / Heating 7: 71 percent / hydrogen chloride / methanol; pyridine / 0.67 h / 190 °C View Scheme

1: 71 percent / dioxane / 1.) 100 min, 2.) reflux, 22 h 2: hydrogen / 10 percent palladium/charcoal / ethanol; H2O / Ambient temperature 3: 32 percent / conc. hydrochloric acid / ethanol; H2O / 2.5 h / Heating 4: 60 percent / 6 N hydrochloric acid / 7.5 h / Heating 5: 27 percent / 10 percent palladium/charcoal / various solvent(s) / 50 h / Heating 6: 71 percent / hydrogen chloride / methanol; pyridine / 0.67 h / 190 °C View Scheme

1: 54 percent / hydrogenchloride / ethanol / 2.5 h / Heating 2: 22.4 percent / 10 percent palladium/carbon / decahydronaphthalene / 6 h / 205 °C 3: 71 percent / hydrogen chloride / methanol; pyridine / 0.67 h / 190 °C View Scheme

1: 92.8 percent / hydrogen / 10 percent palladium/charcoal / ethanol; H2O / 110 h / Ambient temperature 2: 54 percent / hydrogenchloride / ethanol / 2.5 h / Heating 3: 22.4 percent / 10 percent palladium/carbon / decahydronaphthalene / 6 h / 205 °C 4: 71 percent / hydrogen chloride / methanol; pyridine / 0.67 h / 190 °C View Scheme

1: 32 percent / conc. hydrochloric acid / ethanol; H2O / 2.5 h / Heating 2: 60 percent / 6 N hydrochloric acid / 7.5 h / Heating 3: 27 percent / 10 percent palladium/charcoal / various solvent(s) / 50 h / Heating 4: 71 percent / hydrogen chloride / methanol; pyridine / 0.67 h / 190 °C View Scheme

1: hydrogen / 10 percent palladium/charcoal / ethanol; H2O / Ambient temperature 2: 32 percent / conc. hydrochloric acid / ethanol; H2O / 2.5 h / Heating 3: 60 percent / 6 N hydrochloric acid / 7.5 h / Heating 4: 27 percent / 10 percent palladium/charcoal / various solvent(s) / 50 h / Heating 5: 71 percent / hydrogen chloride / methanol; pyridine / 0.67 h / 190 °C View Scheme

1: 27 percent / 10 percent palladium/charcoal / various solvent(s) / 50 h / Heating 2: 71 percent / hydrogen chloride / methanol; pyridine / 0.67 h / 190 °C View Scheme