Efficient Copper-Catalyzed Synthesis of N-Alkylanthranilic Acids via an ortho-Substituent Effect of the Carboxyl Group of 2-Halobenzoic Acids at Room Temperature.

We have developed an efficient copper-catalyzed method for the synthesis of N-alkylanthranilic acids. The protocol uses inexpensive copper(I) iodide/racemic 1,1′-binaphthyl-2,2′-diol (rac-BINOL) as the catalyst/ligand system, readily available 2-halobenzoic acids and aliphatic amines as the starting materials, the coupling reactions were performed at room temperature, and various functionalities in the substrates were tolerated.