ammonium cerium(IV) nitrate in acetonitrile T=0°C; 0.05 h;

hydrogenchloride in tetrahydrofuran; methanol T=100°C;

ammonium cerium(IV) nitrate in water; acetonitrile T=-20°C; 0.0833333 h;

Fremy’s salt in water; acetone T=20°C; 3 h;

1: hydrogen / Pd/C / ethyl acetate; ethanol / 5 h / 20 °C / 760 Torr 2: 1.11 g / potassium nitrosodisulfonate / H2O; acetone / 3 h / 20 °C View Scheme

1: 73 percent / aq. perchloric acid / 2 h / 70 °C 2: 90 percent / K2CO3 / methanol / 3 h / 0 °C 3: 84 percent / K2CO3 / dimethylformamide / 5 h / 20 °C 4: aq. HCl / dioxane / 24 h / 80 °C 5: 1.86 g / K2CO3 / dimethylformamide / 1 h / 60 °C 6: hydrogen / Pd/C / ethyl acetate; ethanol / 5 h / 20 °C / 760 Torr 7: 1.11 g / potassium nitrosodisulfonate / H2O; acetone / 3 h / 20 °C View Scheme

1: 90 percent / K2CO3 / methanol / 3 h / 0 °C 2: 84 percent / K2CO3 / dimethylformamide / 5 h / 20 °C 3: aq. HCl / dioxane / 24 h / 80 °C 4: 1.86 g / K2CO3 / dimethylformamide / 1 h / 60 °C 5: hydrogen / Pd/C / ethyl acetate; ethanol / 5 h / 20 °C / 760 Torr 6: 1.11 g / potassium nitrosodisulfonate / H2O; acetone / 3 h / 20 °C View Scheme

1: 84 percent / K2CO3 / dimethylformamide / 5 h / 20 °C 2: aq. HCl / dioxane / 24 h / 80 °C 3: 1.86 g / K2CO3 / dimethylformamide / 1 h / 60 °C 4: hydrogen / Pd/C / ethyl acetate; ethanol / 5 h / 20 °C / 760 Torr 5: 1.11 g / potassium nitrosodisulfonate / H2O; acetone / 3 h / 20 °C View Scheme

1: 1.86 g / K2CO3 / dimethylformamide / 1 h / 60 °C 2: hydrogen / Pd/C / ethyl acetate; ethanol / 5 h / 20 °C / 760 Torr 3: 1.11 g / potassium nitrosodisulfonate / H2O; acetone / 3 h / 20 °C View Scheme

1: aq. HCl / dioxane / 24 h / 80 °C 2: 1.86 g / K2CO3 / dimethylformamide / 1 h / 60 °C 3: hydrogen / Pd/C / ethyl acetate; ethanol / 5 h / 20 °C / 760 Torr 4: 1.11 g / potassium nitrosodisulfonate / H2O; acetone / 3 h / 20 °C View Scheme