Collect. Czech. Chem. Commun. 1987, 52, 1780-1785

Photoreaction of N-butyl 3,4-dimethoxy-6-nitrobenzamide with butylamine. A model study for lysine-directed photoaffinity labelling

Petr Kuzmič, Libuše Pavlíčková and Milan Souček

Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6


Ultraviolet irradiation of the title compound I in the presence of butylamine gave predominantly products of nucleophilic photosubstitution by the amine, i.e., nitroanilines IIa and IIb. Besides, small amounts of products of hydrolysis (phenol III) and reductive coupling (azoxybenzene IV) were also formed. Comparison of the overall photolysis rate of I with that of 3,4-dimethoxy-1-nitrobenzene (V) indicates a minor loss of reactivity, most probably due to some deviation from coplanarity of the activating nitro group and the aromatic ring.