O-Allylhydroxylamine

PreparationAllyl Bromide (39 mL, 0.46 mol) is added dropwise with stirring to a suspension of anhydrous K2CO3 (43 g) and commercially available N-hydroxyphthalimide (50 g, 0.31 mol) in DMSO (500 mL) at 25 °C. After addition, the mixture is stirred at room temp for 24 h and then poured into cold water (3 L). The precipitate is collected, washed with water, and dried. Recrystallization from EtOH gives Nallyloxyphthalimide (87%), mp 56-57°C. A mixture of N-allyloxyphthalimide (10 g, 0.05 mol), hydrazine hydrate (5 mL, 0.1 mol), and EtOH (100 mL) is refluxed for 2 h and then cooled and poured into 3% aqueous Na2CO3 (500 mL). The solution is extracted with ether. The ether extract is washed with water and then 5 mL ofconc HCl are added. Evaporation gives a solid which is recrystallized from EtOH and ether to afford Oallylhydroxylamine hydrochloride as a white solid (eq 1). The free amine can be liberated by distillation from KOH (bp 80°C) or by treatment with ammonia in situ. It may be conveniently stored as the Nallyloxphthalimide intermediate which is converted to 1-(Aminooxy)-2-propene hydrochloride as needed.