quinoline; hydrogen; Lindlar's catalyst in methanol P=1551.4 Torr; 3 h;

1: 1.) potassium bis(trimethylsilyl)amide / 1.) DMF, 15 min, 2.) DMF, a) 20 deg C, 3 h, b) 40 deg C, 2 h 2: 73 percent / methanolic NH3 / 18 °C 3: 88 percent / H2 / Lindlar catalyst / methanol / 5 h View Scheme

1: 73 percent / methanolic NH3 / 18 °C 2: 88 percent / H2 / Lindlar catalyst / methanol / 5 h View Scheme

1: 54 percent / (CH3)3SiI / CHCl3 / 0.5 h / Heating 2: 69 percent / PrNH2 / 24 h / Heating View Scheme