1973 年 93 巻 9 号 p. 1100-1104
N-Methylacetanilide did not react on Friedel-Crafts acylation but did afford o- and p-nitro compounds (ortho : para ratio, 1 : 6) on mixed acid nitration. Nitration with copper nitrate and acetic anhydride furnished only the p-nitro compound rather than the o-nitro compound as reported previously in the nitration of acetanilide. The bromination of N-methylacetanilide with bromine in acetic acid occurred at para-position as in acetanilide but there precipitated an orange crystals which were an addition compound composed of two moles of p-bromo-N-methylacetanilide and one mole each of bromine and hydrogen bromide (p-BrC6H4N(CH3)Ac)2·HBr3. Several N-methylacetanilide derivatives were synthesized and tested for the formation of bromine addition compounds. When N-methylacetamide group in benzene ring is one, composition of the addition compounds is A2HBr3 (where A represents the N-methylacetanilide derivative), but when two, the composition is A·HBr3 (Fig. 2), similar to that of pyridinium bromide perbromide (C5H5N·HBr)3.