N-Methylacetanilideの置換反応とその誘導体の臭素付加体について

概要

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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-BrC_6H_4N(CH_3)Ac)_2・HBr_3. 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 A_2HBr_3 (where A represents the N-methylacetanilide derivative), but when two, the composition is A・HBr_3 (Fig. 2), similar to that of pyridinium bromide perbromide (C_5H_5N・HBr)_3.
社団法人日本薬学会の論文
1973-09-25