p-Nitrocinnamonitrile → p-Nitrocinnamamidoxime

Participants

Reaction Steps

p-Nitrocinnamonitrile (8.12 g.) was added at 30° 35° to an anhydrous methanolic hydroxylamine solution (320 ml.) prepared by neutralising hydroxylamine hydrochloride (13.00 g.) with methanolic sodium methoxide. The solution was refluxed for 2.5 hr. and left overnight. Removal of the solvent and washing with water left the crude amidoxime, 7.07 g. (74%), m.p. 184-185° (decomp.). Recrystallisation of a sample from ethanol gave p-nitrocinnamamidoxime as yellow needles, m.p. 184° -186° , λmax. (EtOH) 235.5, 265, 344 nm, (ε 10020, 10000, 14800) (Found: C, 51.7; H, 4.7; N, 20.0. C9H9N3O3 requires C, 52.2; H, 4.4; N, 20.3%).

Provenance & Evidence