copper (II) chromite in quinoline; hexane

Catalyst M-Chromium oxide; copper(II) oxide in quinoline T=190 - 195°C; 7.5 h;

1: 1) n-butyllithium / 1) ether, -70 deg C, 6 h; 2) ether, -70 deg C, 12 h 2: Na / methanol / 6 h / 0 °C 3: 55.5 percent / N2 / various solvent(s) / 0.33 h / 110 °C 4: 93 percent / 1) KOH, H2O; 2) 5 N HCl / 1) reflux, 3.5 h; 2) 0 deg C 5: 74 percent / CuO, Cr2O3 / quinoline / 7.5 h / 190 - 195 °C View Scheme

1: Na / methanol / 6 h / 0 °C 2: 55.5 percent / N2 / various solvent(s) / 0.33 h / 110 °C 3: 93 percent / 1) KOH, H2O; 2) 5 N HCl / 1) reflux, 3.5 h; 2) 0 deg C 4: 74 percent / CuO, Cr2O3 / quinoline / 7.5 h / 190 - 195 °C View Scheme

1: 93 percent / 1) KOH, H2O; 2) 5 N HCl / 1) reflux, 3.5 h; 2) 0 deg C 2: 74 percent / CuO, Cr2O3 / quinoline / 7.5 h / 190 - 195 °C View Scheme

1: 55.5 percent / N2 / various solvent(s) / 0.33 h / 110 °C 2: 93 percent / 1) KOH, H2O; 2) 5 N HCl / 1) reflux, 3.5 h; 2) 0 deg C 3: 74 percent / CuO, Cr2O3 / quinoline / 7.5 h / 190 - 195 °C View Scheme

1: 50 percent / Zn, HgCl2, H2O, conc. HCl / toluene / 1 h / Heating 2: 1) n-butyllithium / 1) ether, -70 deg C, 6 h; 2) ether, -70 deg C, 12 h 3: Na / methanol / 6 h / 0 °C 4: 55.5 percent / N2 / various solvent(s) / 0.33 h / 110 °C 5: 93 percent / 1) KOH, H2O; 2) 5 N HCl / 1) reflux, 3.5 h; 2) 0 deg C 6: 74 percent / CuO, Cr2O3 / quinoline / 7.5 h / 190 - 195 °C View Scheme