ammonium formate; Pd/C in ethanol 4 h; Heating / reflux;

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

1: hydroxylamine hydrochloride; sodium hydroxide / ethanol; water / 20 h / |Inert atmosphere; |Reflux 2: sodium; propan-1-ol / toluene / 12 h / |Reflux; |Inert atmosphere 3: tetrahydrofuran / 72 h / 20 °C / |Inert atmosphere 4: hydrogenchloride / methanol; 1,4-dioxane / 2 h / 20 °C / |Inert atmosphere 5: sodium carbonate / water; dichloromethane / 0 - 20 °C / |Inert atmosphere View Scheme

1: hydroxylamine hydrochloride; sodium hydroxide / ethanol; water / 20 h / |Inert atmosphere; |Reflux 2: sodium; propan-1-ol / toluene / 12 h / |Reflux; |Inert atmosphere 3: tetrahydrofuran / 72 h / 20 °C / |Inert atmosphere 4: hydrogenchloride / methanol; 1,4-dioxane / 2 h / 20 °C / |Inert atmosphere 5: sodium carbonate / water; dichloromethane / 0 - 20 °C / |Inert atmosphere 6: phosphorus pentachloride / dichloromethane / 2 h / 0 - 20 °C / |Inert atmosphere 7: dichloromethane; 1,1-dimethylpropan-1-ol / 0 - 20 °C / |Inert atmosphere 8: acetic acid / ethyl acetate / 0.5 h / 80 °C / |Inert atmosphere View Scheme

in ethylene glycol dimethyl ether; ethanol; ethyl acetate

hydrogen; palladium hydroxide on carbon in ethyl acetate P=3102.97 Torr;

hydrogen; palladium dihydroxide in di-tert-butyl dicarbonate; ethyl acetate

1: 91 percent / Hydroxylamine hydrochloride, sodium bicarbonate / aq. ethanol / 0.5 h / 100 °C 2: 66 percent / Sodium, ethanol / 16 h / Heating View Scheme

1: 91 percent / Hydroxylamine hydrochloride, sodium bicarbonate / aq. ethanol / 0.5 h / 100 °C 2: 46 percent / Hydrogen / Platinum oxide / ethanol; acetic acid / 48 h / 2316.8 Torr View Scheme

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