Synthesis of novel 2-(fluoroanilino)-3-(2,4-dinitroanilino) derivatives of 1,4-naphthoquinone

Several novel 2-(fluoroanilino)-3-(2,4-dinitroanilino) derivatives of 1,4-naphthoquinone have been synthesized in good to excellent yields. First, 2-chloro-3-(2,4-dinitroanilino)-1,4-naphthoquinone was prepared in two steps beginning with the reaction of 2,3-dichloro-1,4-naphthoquinone with aniline in the presence of a Lewis acid (CeCl ·7H O). The resulting 2-(anilino)-1,4-naphthoquinone was then nitrated. The strong electron withdrawing effect of the 2,4-dinitroanilino substituent on the naphthoquinone framework facilitated the displacement of the second chlorine atom by a variety of weakly nucleophilic fluoro-substituted anilines under reflux conditions. 3