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

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