All published syntheses of the compound 2-pyridinecarbaldehyde N-oxide are rather difficult or give a low yield. The goal of this research is to develop a more effective and efficient procedure to synthesize 2-pyridinecarbaldehyde N-oxide which is used as a starting reagent for the synthesis of pyridine N-oxide Schiff bases. Aromatic amine N-oxide Schiff bases are promising ligands in creating coordination complexes that can be used as stereospecific catalysts in organic synthesis, new anticancer drugs, or new materials with interesting magnetic properties. Following the commonly used procedure for the synthesis of 2-pyridinecarbaldehyde N-oxide, 2-methylpyridine was oxidized with a mixture of hydrogen peroxide and glacial acetic acid to form 2-methyl pyridine N-oxide. Subsequently, the methyl group of 2-methylpyridine N-oxide was selectively oxidized to aldehyde with selenium dioxide in pyridine. A crude product was purified by fractional recrystallization from toluene. A new procedure utilizes oxidation of 2-pyridinecarbaldehyde protected in a form of diacetal. Several methods of separation of the desired product from the starting material as well as complexation abilities of both will be presented.

Synthesis of 2-pyridinecarbaldehyde N-oxide

255th National Meeting (2018)

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