Metal-Free C-5 Hydroxylation of 8-Aminoquinoline Amide.

Diacetoxyiodobenzene-mediated remote hydroxylation of 8-aminoquinoline amide at the C-5 position has been developed. Various aryl, heteroaryl, and aliphatic carboxamides work well to afford the hydroxylated derivatives in good yields. This protocol is scalable and exhibits high functional group tolerance. Experimental results suggest that the reaction likely proceeds through the single-electron-transfer pathway.