5-(1-Hydroxypropylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione → 2,6-diethyl-4-hydroxy-3-Pyridinecarboxylic acid methyl ester

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Reaction Conditions

Reaction Steps

A mixture of methyl 3-aminopentenoate (7.3 g) and 5-(1-hydroxypropylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione (23.0 g) (obtained as described in J. Org. Chem., 1978, 43, 2087) was heated at 120° C. for 2 hours. The mixture was cooled to ambient temperature and triturated with ether (50 ml). The product was collected by filtration to give methyl 2,6-diethyl-4-oxo-1,4-dihydropyridine-3-carboxylate (5.2 g) as a solid, m.p. 124°-127° C.; NMR (d6 -DMSO): 1.2(t, 6H), 2.3-2.6(m, 4H), 3.7(s, 3H), 5.9(s, 1H), 11.2(s, 1H); mass spectrum (CI, ammonia): 210 (M+H)+ ; microanalysis, found: C, 63.1; H, 7.5; N, 6.7%; C11H15NO3 requires: C, 63.1; H, 7.2; N, 6.7%.

Provenance & Evidence