hydroxylamine hydrochloride; sodium acetate in methanol T=20°C;

sodium acetate in methanol

1: triethylamine / tetrahydrofuran / 70 °C 2: hydroxylamine hydrochloride; sodium carbonate / methanol / 5 h / 0 - 20 °C View Scheme

1.1: hydrogenchloride; water / 1 h / Reflux 1.2: 6 h / 0 - 50 °C 1.3: pH 12 2.1: hydroxylamine hydrochloride; pyridine / ethanol / 18 h / Reflux View Scheme

1.1: hydrogenchloride; water / 1 h / Reflux 1.2: 6 h / 0 - 50 °C 1.3: pH 12 2.1: hydroxylamine hydrochloride; pyridine / ethanol / 18 h / Reflux View Scheme

1.1: sodium; pentan-1-ol / 2 h / Reflux 2.1: sodium carbonate / dichloromethane; water / 2 h / 0 - 20 °C 3.1: phosphorus pentachloride / dichloromethane / 2 h / 10 - 20 °C / Cooling with ice 3.2: 10 - 20 °C 3.3: pH 12 / Cooling with ice 4.1: ammonium formate / palladium 10 on activated carbon / ethanol / 12 h / Reflux; Inert atmosphere View Scheme

1: sodium; propan-1-ol / toluene / 12 h / |Reflux; |Inert atmosphere 2: tetrahydrofuran / 72 h / 20 °C / |Inert atmosphere 3: hydrogenchloride / methanol; 1,4-dioxane / 2 h / 20 °C / |Inert atmosphere 4: sodium carbonate / water; dichloromethane / 0 - 20 °C / |Inert atmosphere 5: phosphorus pentachloride / dichloromethane / 2 h / 0 - 20 °C / |Inert atmosphere 6: dichloromethane; 1,1-dimethylpropan-1-ol / 0 - 20 °C / |Inert atmosphere 7: acetic acid / ethyl acetate / 0.5 h / 80 °C / |Inert atmosphere 8: palladium 10 on activated carbon; hydrogen / methanol / 20 °C / 2585.81 Torr / |Inert atmosphere 9: acetic acid; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 3 h / 0 - 20 °C / |Inert atmosphere View Scheme

1: sodium / toluene; pentan-1-ol / 0.25 h / |Reflux; |Inert atmosphere 2: sodium carbonate / dichloromethane; water / 1 h / 0 - 20 °C / |Inert atmosphere; |Large scale View Scheme

1.1: sodium / toluene; pentan-1-ol / 0.25 h / |Reflux; |Inert atmosphere 2.1: sodium carbonate / dichloromethane; water / 1 h / 0 - 20 °C / |Inert atmosphere; |Large scale 3.1: phosphorus pentachloride / dichloromethane / 4 h / -5 - 20 °C / |Inert atmosphere 3.2: 15.5 h / 10 - 20 °C / |Inert atmosphere 3.3: 2 h / 80 °C / |Inert atmosphere View Scheme

ethanol; sodium 16 h; Heating;