1: With water; sodium hydroxide in ethanol T=50°C; 6 h; 2: With hydrogenchloride in 1,4-dioxane

1.1: hydrogenchloride / 1,4-dioxane / 0.5 h / 50 °C 2.1: pyridine / dichloromethane / 0.5 h 3.1: ammonium formate / palladium 10 on activated carbon / water; industrial methylated spirit / 1 h / Reflux 4.1: hydrogenchloride; sodium nitrite / water / 0 °C 4.2: 0 - 20 °C 5.1: sodium hydroxide; water / ethanol / 6 h / 50 °C View Scheme

1.1: pyridine / dichloromethane / 0.5 h 2.1: ammonium formate / palladium 10 on activated carbon / water; industrial methylated spirit / 1 h / Reflux 3.1: hydrogenchloride; sodium nitrite / water / 0 °C 3.2: 0 - 20 °C 4.1: sodium hydroxide; water / ethanol / 6 h / 50 °C View Scheme

1.1: ammonium formate / palladium 10 on activated carbon / water; industrial methylated spirit / 1 h / Reflux 2.1: hydrogenchloride; sodium nitrite / water / 0 °C 2.2: 0 - 20 °C 3.1: sodium hydroxide; water / ethanol / 6 h / 50 °C View Scheme

1.1: hydrogenchloride; sodium nitrite / water / 0 °C 1.2: 0 - 20 °C 2.1: sodium hydroxide; water / ethanol / 6 h / 50 °C View Scheme