quinoline; hydrogen; Lindlar's catalyst in ethanol

1: 1.) LiNH2, liq. NH3, HMPA / 1.) -33 deg C, 2 h, 2.) THF, -33 deg C, 6 h 2: 90 percent / PTSA / methanol; H2O / 12 h / Ambient temperature 3: 88.8 percent / DMAP / pyridine / 8 h / Ambient temperature 4: 85 percent / H2, quinoline / Lindlar catalyst / ethanol View Scheme

1: 88.8 percent / DMAP / pyridine / 8 h / Ambient temperature 2: 85 percent / H2, quinoline / Lindlar catalyst / ethanol View Scheme

1: 72.1 percent / NaNH2, 1,3-diaminopropane / 4 h / 80 °C 2: 85 percent / PTSA / CH2Cl2 / 8 h / Ambient temperature 3: 1.) LiNH2, liq. NH3, HMPA / 1.) -33 deg C, 2 h, 2.) THF, -33 deg C, 6 h 4: 90 percent / PTSA / methanol; H2O / 12 h / Ambient temperature 5: 88.8 percent / DMAP / pyridine / 8 h / Ambient temperature 6: 85 percent / H2, quinoline / Lindlar catalyst / ethanol View Scheme

1: 85 percent / PTSA / CH2Cl2 / 8 h / Ambient temperature 2: 1.) LiNH2, liq. NH3, HMPA / 1.) -33 deg C, 2 h, 2.) THF, -33 deg C, 6 h 3: 90 percent / PTSA / methanol; H2O / 12 h / Ambient temperature 4: 88.8 percent / DMAP / pyridine / 8 h / Ambient temperature 5: 85 percent / H2, quinoline / Lindlar catalyst / ethanol View Scheme

1: 90 percent / PTSA / methanol; H2O / 12 h / Ambient temperature 2: 88.8 percent / DMAP / pyridine / 8 h / Ambient temperature 3: 85 percent / H2, quinoline / Lindlar catalyst / ethanol View Scheme

1: acetic acid / 10 h / 50 °C 2: H2 / P-2 Ni View Scheme

1: 85percent hydrazine hydrate / butan-1-ol / Heating 2: O2, CuCl / pyridine 3: acetic acid / 10 h / 50 °C 4: H2 / P-2 Ni View Scheme

1: (AcO)2Cu / acetic acid; H2O / 0.67 h / Heating 2: 85percent hydrazine hydrate / butan-1-ol / Heating 3: O2, CuCl / pyridine 4: acetic acid / 10 h / 50 °C 5: H2 / P-2 Ni View Scheme

1: O2, CuCl / pyridine 2: acetic acid / 10 h / 50 °C 3: H2 / P-2 Ni View Scheme