copper (II) chromite in quinoline

Catalyst M-Chromium oxide; copper(II) oxide in quinoline 13 h;

1: 1) NaOH / 1) H2O, reflux, 15 min; 2) H2O, reflux, 50 min 2: 1) H3PO4, P2O5 / 1) benzene, 4 h, reflux; 2) benzene 12 h, reflux 3: 82 percent / 3 percent p-toluenesulfonic acid / toluene / 7 h / Heating 4: 1) n-BuLi / 1) ether, -70 deg C, 6 h; 2) ether, 12 h, -70 deg C 5: Na / methanol / 168 h / 0 °C 6: xylene / 3 h / Heating 7: conc. HCl, H2O / ethanol / 18 h 8: 93 percent / KOH, H2O 9: 54 percent / CuO, Cr2O3 / quinoline / 13 h View Scheme

1: Br2 2: 1) NaOH / 1) H2O, reflux, 15 min; 2) H2O, reflux, 50 min 3: 1) H3PO4, P2O5 / 1) benzene, 4 h, reflux; 2) benzene 12 h, reflux 4: 82 percent / 3 percent p-toluenesulfonic acid / toluene / 7 h / Heating 5: 1) n-BuLi / 1) ether, -70 deg C, 6 h; 2) ether, 12 h, -70 deg C 6: Na / methanol / 168 h / 0 °C 7: xylene / 3 h / Heating 8: conc. HCl, H2O / ethanol / 18 h 9: 93 percent / KOH, H2O 10: 54 percent / CuO, Cr2O3 / quinoline / 13 h View Scheme

1: 1) H3PO4, P2O5 / 1) benzene, 4 h, reflux; 2) benzene 12 h, reflux 2: 82 percent / 3 percent p-toluenesulfonic acid / toluene / 7 h / Heating 3: 1) n-BuLi / 1) ether, -70 deg C, 6 h; 2) ether, 12 h, -70 deg C 4: Na / methanol / 168 h / 0 °C 5: xylene / 3 h / Heating 6: conc. HCl, H2O / ethanol / 18 h 7: 93 percent / KOH, H2O 8: 54 percent / CuO, Cr2O3 / quinoline / 13 h View Scheme

1: 1) n-BuLi / 1) ether, -70 deg C, 6 h; 2) ether, 12 h, -70 deg C 2: Na / methanol / 168 h / 0 °C 3: xylene / 3 h / Heating 4: conc. HCl, H2O / ethanol / 18 h 5: 93 percent / KOH, H2O 6: 54 percent / CuO, Cr2O3 / quinoline / 13 h View Scheme

1: Na / methanol / 168 h / 0 °C 2: xylene / 3 h / Heating 3: conc. HCl, H2O / ethanol / 18 h 4: 93 percent / KOH, H2O 5: 54 percent / CuO, Cr2O3 / quinoline / 13 h View Scheme

1: 93 percent / KOH, H2O 2: 54 percent / CuO, Cr2O3 / quinoline / 13 h View Scheme

1: conc. HCl, H2O / ethanol / 18 h 2: 93 percent / KOH, H2O 3: 54 percent / CuO, Cr2O3 / quinoline / 13 h View Scheme

1: 82 percent / 3 percent p-toluenesulfonic acid / toluene / 7 h / Heating 2: 1) n-BuLi / 1) ether, -70 deg C, 6 h; 2) ether, 12 h, -70 deg C 3: Na / methanol / 168 h / 0 °C 4: xylene / 3 h / Heating 5: conc. HCl, H2O / ethanol / 18 h 6: 93 percent / KOH, H2O 7: 54 percent / CuO, Cr2O3 / quinoline / 13 h View Scheme