Photodegradation of Amino- and Hydroxyphenazone in Acetone

Article abstract of DOI:10.1002/ardp.19833161206

The photochemical degradation of aminophenazone in acetone leads to 2-<1-(methylimino)ethyl-4-oxopent-2-enoic anilide (7), 6-methyl-2-<1-(methylimino)ethyl>-4-oxohepta-2,5-dienoic anilide (9), N,N-dimethyl-N'-phenyl oxamide (10) and N,N-dimethyl-N'-phenylurea (11).In addition to the last two products, oxanilide and N-methyl-N'-phenyl oxamide are obtained, when the irradiation is carried out in acetonitrile. 6-Methyl-2-<1-(methylimino)ethyl>-4-oxohepta-2,5-dienoic anilide, oxanilide and N-methyl-N'-phenyl oxamide are formed as a result of hydroxyphenazone photolysis in acetone.The degradation mechanism is discussed.