1: With hydrogenchloride; water; acetic acid T=110°C; 16 h; Sealed tube; 2: With potassium hydroxide in water Product distribution / selectivity;

1.1: sodium hydrogencarbonate / water; tetrahydrofuran / 0 - 20 °C 2.1: hydrogen / palladium 10 on activated carbon / methanol / 16 h / 20 °C 3.1: hydrogenchloride; sodium nitrite / water / 0.5 h / 0 °C 3.2: 0 - 20 °C 4.1: sulfuric acid / 18 h / 105 °C 4.2: 20 °C / pH 13 5.1: triethylamine / anhydrous dichloroethane / Reflux 6.1: diethylamino-sulfur trifluoride / dichloromethane / -78 - 20 °C 7.1: hydrogenchloride; water; acetic acid / 16 h / 110 °C / Sealed tube View Scheme

1.1: hydrogen / palladium 10 on activated carbon / methanol / 16 h / 20 °C 2.1: hydrogenchloride; sodium nitrite / water / 0.5 h / 0 °C 2.2: 0 - 20 °C 3.1: sulfuric acid / 18 h / 105 °C 3.2: 20 °C / pH 13 4.1: triethylamine / anhydrous dichloroethane / Reflux 5.1: diethylamino-sulfur trifluoride / dichloromethane / -78 - 20 °C 6.1: hydrogenchloride; water; acetic acid / 16 h / 110 °C / Sealed tube View Scheme

1.1: hydrogenchloride; sodium nitrite / water / 0.5 h / 0 °C 1.2: 0 - 20 °C 2.1: sulfuric acid / 18 h / 105 °C 2.2: 20 °C / pH 13 3.1: triethylamine / anhydrous dichloroethane / Reflux 4.1: diethylamino-sulfur trifluoride / dichloromethane / -78 - 20 °C 5.1: hydrogenchloride; water; acetic acid / 16 h / 110 °C / Sealed tube View Scheme

1.1: sulfuric acid / 18 h / 105 °C 1.2: 20 °C / pH 13 2.1: triethylamine / anhydrous dichloroethane / Reflux 3.1: diethylamino-sulfur trifluoride / dichloromethane / -78 - 20 °C 4.1: hydrogenchloride; water; acetic acid / 16 h / 110 °C / Sealed tube View Scheme

1: diethylamino-sulfur trifluoride / dichloromethane / -78 - 20 °C 2: hydrogenchloride; water; acetic acid / 16 h / 110 °C / Sealed tube View Scheme