1,3-Dinitrobenzene (la) and some simple monosubstituted derivatives (lb-g) were aminated with a liquid methylamine solution of potassium permanganate (LMA/PP) to give the corresponding mono-and bis(methy1amino)-substituted compounds (3a-e and 4a). 1,2-Dinitrobenzene ( l i ) was aminated with LMA/PP to give 2-(rnethylamino)-l-nitrobenzene (3f) in high yield. The intermediacy of 4-(methylamino) a-adducts of 1,3-dinitrobenzene (2a), 2-chloro-(2b) and 2-amino-1,3-dinitrobenzene (2c) was established by ' H-NMR spectroscopy. Quantum-chemical calculations for the dinitrobenzenes suggest that, in general, the experimentally observed regioselectivity of the methylamination is satisfactorily described by frontier molecular orbital (FMO) interaction of the reagents.

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2‐Amino‐6‐hydroxypyridin (I) reagiert mit Glycerin (II) unter den Bedingungen der Skraupschen Synthese zu 2‐Hydroxy‐1 ,8‐naphthyridin (III).