quinoline; hydrogen; Pd-BaSO4 in ethanol T=20°C; 7 h;

1.1: n-butylmagnesium chloride / tetrahydrofuran / 1.33 h / cooling 1.2: anhydrous cerium (III) chloride / tetrahydrofuran / 1.5 h / 0 °C 1.3: 84 percent / tetrahydrofuran / 1.5 h / 0 °C 2.1: 91 percent / quinoline; H2 / Pd/BaSO4 / ethanol / 7 h / 20 °C View Scheme

1: imidazole / CH2Cl2 / 1 h / 20 °C 2: 2.41 g / m-chloroperbenzoic acid / CH2Cl2 / 20 °C 3: 99 percent / TBAF / tetrahydrofuran / 1 h / 20 °C 4: 94 percent / PPh3; DEAD / toluene; tetrahydrofuran / 1.5 h / 20 °C 5: 95 percent / sodium methoxide / methanol / 1 h / Heating 6: 83 percent / PPh3; DEAD / tetrahydrofuran / 1 h / 20 °C 7: 90 percent / ammonia / methanol / 80 °C 8: 87 percent / tributyltin hydride; AIBN / toluene / 10 h / Heating View Scheme