2,3-dicyano-5,6-dichloro-p-benzoquinone in benzene 3.5 h; Heating;

1: Et3N / pyridine / 1.33 h / 45 - 50 °C 2: 50percent aq. KOH / pyridine / 0.33 h / 20 °C 3: 99 percent / 5percent aq. KOH / ethanol / 5 h / Heating 4: 99 percent / copper chromite / quinoline / 5 h / Heating 5: 96 percent / DDQ / benzene / 3.5 h / Heating View Scheme

1: 96 percent / POCl3 / dimethylformamide / 1) 0-5 deg C, 1 h, 2) r.t., 15 h, 3) 45-50 deg C, 1 h 2: Et3N / pyridine / 1.33 h / 45 - 50 °C 3: 50percent aq. KOH / pyridine / 0.33 h / 20 °C 4: 99 percent / 5percent aq. KOH / ethanol / 5 h / Heating 5: 99 percent / copper chromite / quinoline / 5 h / Heating 6: 96 percent / DDQ / benzene / 3.5 h / Heating View Scheme

1: 99 percent / copper chromite / quinoline / 5 h / Heating 2: 96 percent / DDQ / benzene / 3.5 h / Heating View Scheme

1: 99 percent / 5percent aq. KOH / ethanol / 5 h / Heating 2: 99 percent / copper chromite / quinoline / 5 h / Heating 3: 96 percent / DDQ / benzene / 3.5 h / Heating View Scheme

iodine in cyclohexane 4 h; Irradiation;