1: hydroxylamine hydrochloride; pyridine / ethanol / 20 °C / Inert atmosphere 2: thionyl chloride / tetrahydrofuran / 0 - 20 °C 3: hydrogenchloride; water / tetrahydrofuran / 1 h / 25 °C View Scheme

1: With copper(l) chloride in ethanol T=20°C; 2 h; Inert atmosphere; 2: With sodium tetrahydroborate in ethanol T=20°C; Inert atmosphere; 3: With hydrogenchloride in water T=20°C; Overall yield = 90 percent; regioselective reaction;

1: With sodium dithionite; sodium hydrogencarbonate in water; toluene 3 h; Reflux; 2: With hydrogenchloride in water; toluene T=20°C; Overall yield = 77 percent; regioselective reaction;

1: With copper(l) chloride in ethanol T=20°C; 2 h; Inert atmosphere; 2: With sodium tetrahydroborate in ethanol T=20°C; Inert atmosphere; 3: With hydrogenchloride in water T=20°C; Overall yield = 90 percent; regioselective reaction;