Catalyst M-Chromium oxide; copper(II) oxide in quinoline T=190 - 195°C; 4 h;

1: 1) n-butyllithium / 1) ether, -50 deg C, 6 h; 2) ether, -50 deg C, 12 h 2: Na / methanol / 6 h / 0 °C 3: 38 percent / N2 / xylene / 5 h / Heating 4: 98 percent / 1) KOH, H2O; 2) 5 N HCl / 1) reflux, 1.5 h, MeOH; 2) 0 deg C, MeOH 5: 60 percent / CuO, Cr2O3 / quinoline / 4 h / 190 - 195 °C View Scheme

1: Na / methanol / 6 h / 0 °C 2: 38 percent / N2 / xylene / 5 h / Heating 3: 98 percent / 1) KOH, H2O; 2) 5 N HCl / 1) reflux, 1.5 h, MeOH; 2) 0 deg C, MeOH 4: 60 percent / CuO, Cr2O3 / quinoline / 4 h / 190 - 195 °C View Scheme

1: 98 percent / 1) KOH, H2O; 2) 5 N HCl / 1) reflux, 1.5 h, MeOH; 2) 0 deg C, MeOH 2: 60 percent / CuO, Cr2O3 / quinoline / 4 h / 190 - 195 °C View Scheme

1: 38 percent / N2 / xylene / 5 h / Heating 2: 98 percent / 1) KOH, H2O; 2) 5 N HCl / 1) reflux, 1.5 h, MeOH; 2) 0 deg C, MeOH 3: 60 percent / CuO, Cr2O3 / quinoline / 4 h / 190 - 195 °C View Scheme

1: 47 percent / Zn, HgCl2, H2O, conc. HCl / toluene / 1 h / Heating 2: 1) n-butyllithium / 1) ether, -50 deg C, 6 h; 2) ether, -50 deg C, 12 h 3: Na / methanol / 6 h / 0 °C 4: 38 percent / N2 / xylene / 5 h / Heating 5: 98 percent / 1) KOH, H2O; 2) 5 N HCl / 1) reflux, 1.5 h, MeOH; 2) 0 deg C, MeOH 6: 60 percent / CuO, Cr2O3 / quinoline / 4 h / 190 - 195 °C View Scheme