Hydroxylamine → HCID 54380485, compound

Participants

Reaction Steps

A solution of hydroxylamine prepared from hydroxylamine hydrochloride (8.34 g.) in methanol (150 ml.) by neutralisation with sodium methoxide was added to o-nitrocinnamonitrile (6.96 g.) (S. Malinowski, Roczniki Chem., 1952, 26, 85) and the mixture was refluxed for 2 hr., then evaporated to ca. 15 ml. under reduced pressure. Ethyl acetate (150 ml.) was added, and the solution was extracted with 2N-hydrochloric acid (2 × 150 ml.). The acid extracts were neutralised with solid sodium hydrogen carbonate, giving a solid (3.3 g., 40%). Recrystallisation from aqueous methanol gave o-nitrocinnamamidoxime, m.p. 173°, λmax. 236, 265 nm, (ε 17150, 14700) (Found: C, 52.4; H, 4.5; N, 20.05. C9H9N3O3 requires C, 52.2; H, 4.4; N, 20.3%).

Provenance & Evidence