A Convenient One-Pot Synthesis of N-Alkylanilines from Benzanilides

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Abstract
The direct synthesis of secondary amines from the corresponding primary amines by alkylation has been widely used. The major drawback, however, consists of polyalkylation. Several procedures exist for the solution of the problem. Some of the early methods involve reduction3, or alkylative hydrolysis4 of Schiff base. Other methods include acid hydrolysis of alkylated formanilides prepared from primary aromatic amine and trialkyl orthoformate5, or acid hydrolysis of N-alkylated phosphinamides6, or zinc cleavage of N-alkylated phenacylsulfonamides7, or reductive deprotection of N-alkylated trifluoromethanesulfonamides7. This latter method is analogous to the Gabriel synthesis of

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