1: H2O, sodium nitrate / diethyl ether / 8 h / Ambient temperature; pH 3.8, other amine, other pH 2: 1) diisobutylaluminium hydride, 2) HCl / 1) toluene, - 78 deg C, 5 min, 2) methanol, reflux, 1 h 3: H2O, NaOH / 1 h / 25 °C / Irradiation View Scheme

sodium nitrate; water in diethyl ether 8 h; Ambient temperaturepH 3.8; Yield given;

1: H2O, sodium nitrate / diethyl ether / 8 h / Ambient temperature; pH 3.8, other amine, other pH 2: 1) diisobutylaluminium hydride, 2) HCl / 1) toluene, - 78 deg C, 5 min, 2) methanol, reflux, 1 h 3: H2O, NaOH / 1 h / 25 °C / Irradiation View Scheme

sodium nitrate; water in diethyl ether 8 h; Ambient temperaturepH 3.8; Yield given;

1: With lithium aluminium tetrahydride in diethyl ether 5 h; Reflux; 2: With water in diethyl ether T=0°C; 3: With hydrogenchloride in 1,4-dioxane

1: With lithium aluminium tetrahydride 2: With hydrogenchloride in diethyl ether

Yield given. Multistep reaction;