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

HRID 487379Notes

Reaction equation

HRID 487379 reaction equation
[NH2:1][C:2]([CH2:8][CH3:9])=[CH:3][C:4]([O:6][CH3:7])=[O:5].O[C:11](=[C:14]1C(=O)OC(C)(C)[O:16][C:15]1=O)[CH2:12][CH3:13]>>[CH2:8]([C:2]1[NH:1][C:11]([CH2:12][CH3:13])=[CH:14][C:15](=[O:16])[C:3]=1[C:4]([O:6][CH3:7])=[O:5])[CH3:9]

Participants

3

Reactant 2

HCID 547061775-(1-Hydroxypropylidene)-2,2-dimethyl-1,3-dioxane-4,6-dioneHCID 57860398Methyl 3-aminopent-2-enoate

Product 1

HCID 149504762,6-diethyl-4-hydroxy-3-Pyridinecarboxylic acid methyl esterYield 44%

Conditions

Temperature
120 °C

Procedure

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%.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. customtriturated with ether (50 ml)
  3. filtrationThe product was collected by filtration

Sources & evidence

ORD record
ord-4f55ab9714e54fc7b88ed467a1eaa0f0
Source dataset
uspto-grants-1994_03
Patent number
US05294620

Reaction notes

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