Pearlman's catalist; hydrogen in ethanol; ethyl acetate P=760.051 Torr;

1: 202 mg / KOH / ethanol / 20 °C 2: H3PO4 / ethanol / 16 h / Heating 3: 53 mg / 2,3-dichloro-5,6-dicyanobenzoquinone / dioxane / 8 h / Heating 4: 13 mg / hydrogen / Pd/C / methanol / 0.5 h / 2068.65 Torr View Scheme

1: 53 mg / 2,3-dichloro-5,6-dicyanobenzoquinone / dioxane / 8 h / Heating 2: 13 mg / hydrogen / Pd/C / methanol / 0.5 h / 2068.65 Torr View Scheme

1: 202 mg / KOH / ethanol / 20 °C 2: H3PO4 / ethanol / 16 h / Heating 3: 53 mg / 2,3-dichloro-5,6-dicyanobenzoquinone / dioxane / 8 h / Heating 4: 13 mg / hydrogen / Pd/C / methanol / 0.5 h / 2068.65 Torr View Scheme

1: 1.8 g / KOH, pyridine / pyridine / 3 h 2: 1.5 g / fused sodium acetate, glacial acetic acid / 4 h / Heating 3: H2 / 10percent Pd/C View Scheme

1: 2.2 g / pyridine / 1 h / Heating 2: 1.8 g / KOH, pyridine / pyridine / 3 h 3: 1.5 g / fused sodium acetate, glacial acetic acid / 4 h / Heating 4: H2 / 10percent Pd/C View Scheme

1: 1.5 g / fused sodium acetate, glacial acetic acid / 4 h / Heating 2: H2 / 10percent Pd/C View Scheme

1: boron trichloride / dichloromethane / 3 h / -78 - -15 °C 2: triethylamine / dichloromethane 3: potassium tert-butylate / tetrahydrofuran / Reflux 4: toluene-4-sulfonic acid / water; benzene / Reflux 5: Pearlman's catalist; hydrogen / ethanol; ethyl acetate / 760.05 Torr View Scheme

1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane 2: iron (III) acetylacetonate / tetrahydrofuran / 0 - 20 °C 3: boron trichloride / dichloromethane / 3 h / -78 - -15 °C 4: triethylamine / dichloromethane 5: potassium tert-butylate / tetrahydrofuran / Reflux 6: toluene-4-sulfonic acid / water; benzene / Reflux 7: Pearlman's catalist; hydrogen / ethanol; ethyl acetate / 760.05 Torr View Scheme

1: water; sodium hydroxide / ethanol / 10 h / 70 °C 2: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane 3: iron (III) acetylacetonate / tetrahydrofuran / 0 - 20 °C 4: boron trichloride / dichloromethane / 3 h / -78 - -15 °C 5: triethylamine / dichloromethane 6: potassium tert-butylate / tetrahydrofuran / Reflux 7: toluene-4-sulfonic acid / water; benzene / Reflux 8: Pearlman's catalist; hydrogen / ethanol; ethyl acetate / 760.05 Torr View Scheme