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

HRID 1769071Notes

Reaction equation

HRID 1769071 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-amino-2-pentenoate (7.3 g) and 5-(1-hydroxypropylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione (23.0 g) was heated at 120° C. for 2 hours. The residue was cooled to ambient temperature, triturated with ether and the solid collected by filtration to give methyl 2,6-diethyl-1,4-dihydro-4-oxopyridine-3carboxylate (5.2 g) as a pale yellow solid, m.p. 124°-127° C.; NMR (d6 -DMSO): 1.2(t,6H), 2.3-2.6(m,4H), 3.7(s,3H), 6.3(s,1H); mass spectrum (chemical ionisation, ammonia): 210 (M+H)+.

Workup

  1. temperatureThe residue was cooled to ambient temperature
  2. customtriturated with ether
  3. filtrationthe solid collected by filtration

Sources & evidence

ORD record
ord-ec81dc6e55c04ec0a909de365f2646d1
Source dataset
uspto-grants-1995_01
Patent number
US05380730

Reaction notes

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