Abstract
DOEBNER'S reaction has been known since 1887 (ref. 1); it consists of the synthesis of quinoline-4-carboxylic acids, the starting materials being an aromatic amine, an aldehyde and pyruvic acid. It was thought that the reaction with 2-amino pyridine would lead to the formation of 1,8-naphthyridine-4-carboxylic acids2, but this was later found to be incorrect. The work of Allen et al. has established that 2-amino pyridine, benzaldehyde and pyruvic acid form a condensation product without cyclization to 1,8-naphthyridine-4-carboxylic acid3. The product was identified as γ-pyridyl-amino-γ-phenyl-α-oxo-butyric acid. The result of the present investigation of Doebner's reaction using 6-methyl-2-amino pyridine agrees with that of Allen et al. It was found that 6-methyl-2-amino pyridine reacts with an aldehyde and pyruvic acids according to the scheme proposed by Allen et al.3. In one representative experiment, 5.4 g (0.05 mole) of 6-methyl-2-amino pyridine was dissolved in 75 ml. of ethyl alcohol in a round bottom flask with three necks equipped with a condenser, a mechanical stirrer and a separatory funnel. The mixture was warmed until all the pyridine went into solution. 7.6 g (0.05 mole) of vanillin was then added and heating was continued. The solution became yellow immediately. At the same time, 4.4 g (0.05 mole) of freshly distilled pyruvic acid was added dropwise through the separatory funnel over a period of 15 min. The mixture was further refluxed for 10 min.
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References
Doebner, O., Ann., 242, 265 (1887).
Mazza, F. P., and Migliardi, C., Atti. Accad. Sci. Torino, 75, 438 (1940).
Allen, C. F. H., et al., J. Org. Chem., 16, 17 (1951).
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NITIDANDHAPRABHAS, O. Doebner's Reaction with 6-Methyl-2-amino Pyridine. Nature 212, 504–505 (1966). https://doi.org/10.1038/212504b0
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DOI: https://doi.org/10.1038/212504b0
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