1: 99 percent / quinoline, hydrogen / Lindlar catalyst / ethyl acetate / 3 h 2: 83 percent / propionic acid / xylene / Heating 3: 97 percent / LiAlH4 / tetrahydrofuran / 1 h / Ambient temperature 4: 277 mg / pyridine / 2 h / Ambient temperature 5: 187 mg / LiAlH4 / tetrahydrofuran / 2 h / Ambient temperature 6: p-TsOH*H2O / dioxane; H2O / 3 h / Heating View Scheme

1: 99 percent / quinoline, hydrogen / Lindlar catalyst / ethyl acetate / 3 h 2: 83 percent / propionic acid / xylene / Heating 3: 100 percent / hydrogen / 10percent Pd/C / ethyl acetate / Ambient temperature 4: LiAlH4 / tetrahydrofuran / Ambient temperature 5: pyridine / Ambient temperature 6: LiAlH4 / tetrahydrofuran / 2 h / Ambient temperature 7: p-TsOH*H2O / dioxane; H2O / 3 h / Heating View Scheme