quinoline; hydrogen; Lindlar's catalyst in ethyl acetate Ambient temperature;

Multi-step reaction with 4 steps 1.1: n-BuLi / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / -78 - -30 °C1.2: 2.12 g / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / 12 h / 20 °C2.1: 1.97 g / KNH(CH2)3NH2 / 0.5 h / 20 °C3.1: n-BuLi / tetrahydrofuran; petroleum ether; hexamethylphosphoric acid triamide / -78 - -30 °C3.2: 390 mg / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / 12 h / 20 °C4.1: 310 mg / CrO3; aq. H2SO4 / acetone / 0.5 h / -10 °C