pyridine T=20°C; 3 h;

1: 95 percent / H2 / Pd-C / dimethylformamide / 20 °C 2: 53 percent / pyridine / 3 h / 20 °C View Scheme

1: 51 percent / NaH / tetrahydrofuran / 4 h / Heating 2: 54 percent / I2; pyridine / 9 h / 120 °C 3: 95 percent / H2 / Pd-C / dimethylformamide / 20 °C 4: 53 percent / pyridine / 3 h / 20 °C View Scheme

1: 54 percent / I2; pyridine / 9 h / 120 °C 2: 95 percent / H2 / Pd-C / dimethylformamide / 20 °C 3: 53 percent / pyridine / 3 h / 20 °C View Scheme

1: 56 percent / KOH / ethanol; H2O / 5 h / Heating 2: 51 percent / NaH / tetrahydrofuran / 4 h / Heating 3: 54 percent / I2; pyridine / 9 h / 120 °C 4: 95 percent / H2 / Pd-C / dimethylformamide / 20 °C 5: 53 percent / pyridine / 3 h / 20 °C View Scheme

1: 1.0 g / KOH / aq. ethanol / Ambient temperature 2: 450 mg / 85percent H3PO4 / ethanol / 50 h / Heating 3: 350 mg / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / dioxane / 10 h / Heating 4: 120 mg / H2 / Pd-C / ethyl acetate 5: AcONa / 1 h / Heating View Scheme

1: 350 mg / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / dioxane / 10 h / Heating 2: 120 mg / H2 / Pd-C / ethyl acetate 3: AcONa / 1 h / Heating View Scheme