2,3-dicyano-5,6-dichloro-p-benzoquinone in benzene 0.5 h; Heating;

potassium carbonate in methanol 1.5 h; Heating;

1: 0.7 g / K2CO3, KI / acetone / 20 h / Heating 2: 0.15 g / N,N-dimethylaniline / 6 h / 100 - 120 °C View Scheme

2,3-dicyano-5,6-dichloro-p-benzoquinone in benzene 8 h; Heating;

N,N-dimethyl-aniline T=100 - 120°C; 6 h;

1: 0.15 g / BF3.Et2O / dioxane / 1 h / 35 - 40 °C 2: 0.2 g / Zn/cc. HCl / ethanol / 0.5 h / Heating 3: 0.4 g / DDQ / benzene / 0.5 h / Heating View Scheme

1: 0.2 g / Zn/cc. HCl / ethanol / 0.5 h / Heating 2: 0.4 g / DDQ / benzene / 0.5 h / Heating View Scheme

1: 90 percent orthophosphoric acid / xylene / 20 h / 30 - 35 °C 2: 0.18 g / DDQ / benzene / 8 h / Heating View Scheme

1: 90 percent orthophosphoric acid / xylene / 20 h / 30 - 35 °C 2: 0.18 g / DDQ / benzene / 8 h / Heating View Scheme

1: 1.) polyphosphoric acid, 2.) potassium carbonate / 1.) dioxane, 60 deg C, 3 h, 2.) acetone, reflux, 50 h 2: 64 percent / potassium carbonate / acetone / 2 h / Heating 3: 93 percent / potassium carbonate / acetone / 4 h / Heating 4: 70 percent / NaBH4, PdCl2 / tetrahydrofuran; H2O / 1.5 h / 0 - 5 °C 5: 92 percent / toluene-p-sulfonic acid / toluene / 0.33 h / Heating 6: 95 percent / potassium carbonate / methanol / 1.5 h / Heating View Scheme