Abstract
Abstract3‐, 5‐, 6‐, 7‐ and 8‐nitroquinoline as well as 5,7‐ and 6,8‐dinitroquinoline are methylaminated with a liquid methylamine solution of potassium permanganate (LMA/PP) to the corresponding mono‐ and bis(methylamino)‐substituted compounds. 2‐Nitroquinoline is aminated with LMA/PP to 2‐(methylamino)quinoline. The intermediate methylamino σ‐adducts of 3‐nitro‐ and 5,7‐ and 6,8‐dinitroquinoline are detected by 1H‐NMR spectroscopy. Quantum chemical calculations for the mononitroquinolines suggest that the experimentally observed regioselectivity of the methylamination is controlled by an interaction of frontal molecular orbitals (FMO) of the reagents.
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