Abstract
A novel and highly regioselective Friedel-Crafts alkylation, producing p-alkyl 3,5-dimethoxyanilines by the reaction of aldehydes with 3,5-dimethoxyaniline in the presence of trifluoroacetic acid and triethylsilane as reducing agent is reported. This procedure is lauded by its high regioselectivity, simplicity, and adaptability to aromatic, heteroaromatic, and aliphatic aldehydes. This reaction represents a useful way to prepare a variety of 4-substituted 3,5-dimethoxyanilines of potential pharmacological interest.
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