Acrolein → 2,3-Diethyl 2,3-pyridinedicarboxylate

HRID 1709308Notes

Reaction equation

HRID 1709308 reaction equation
[NH2:1][CH:2]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH:14]([CH:16]=[CH2:17])=O>C(O)CCC.C1(C)C=CC(S(O)(=O)=O)=CC=1>[N:1]1[CH:17]=[CH:16][CH:14]=[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:2]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

5

Reactant 2

HCID 7847Acrolein2×HCID 423728Aspartic acid, 1,4-diethyl ester

Product 1

HCID 108895172,3-Diethyl 2,3-pyridinedicarboxylateYield 72.9%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 2631-ButanolSolvent

Procedure

Diethyl 1-amino-1,2-ethylenedicarboxylate (1.0 g) and acrolein monomer (0.39 g) are dissolved in n-butanol (10 ml), and thereto is added p-toluenesulfonic acid (20 mg). The mixture is refluxed for 10 hours, and thereto is added additional acrolein monomer (0.1 g), and the mixture is refluxed for 5 hours (the degree of reaction of aminodiester is 91%). After distilling off the solvent, the residue is distilled under reduced pressure to give diethyl pyridine-2,3-dicarboxylate (0.86 g, 72.3%). The product has a boiling point of 135°-145° C. (3 Torr) and a purity of 96.4% by gas chromatographic analysis.

Workup

  1. temperatureThe mixture is refluxed for 10 hours
  2. temperaturethe mixture is refluxed for 5 hours (
  3. distillationAfter distilling off the solvent
  4. distillationthe residue is distilled under reduced pressure

Sources & evidence

ORD record
ord-a5ec69ac094a46d8b89929ca451f8c9c
Source dataset
uspto-grants-1990_08
Patent number
US04948896

Reaction notes

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