Diethyl 2-(ethoxymethylidene)-3-oxobutanedioate → Diethyl 5-acetyl-1,6-dihydro-6-oxo-2,3-pyridinedicarboxylate

HRID 2073974Notes

Reaction equation

HRID 2073974 reaction equation
C([O-])(=O)C.[Na+].[CH2:6]([O:8][C:9](=[O:22])[C:10](=[CH:18]OCC)[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=O)[CH3:7].[C:23]([NH2:29])(=[O:28])[CH2:24][C:25]([CH3:27])=[O:26]>C(O)C>[C:25]([C:24]1[C:23](=[O:28])[NH:29][C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:10]([C:9]([O:8][CH2:6][CH3:7])=[O:22])[CH:18]=1)(=[O:26])[CH3:27]

Participants

5

Reactant 3

HCID 40590Diethyl 2-(ethoxymethylidene)-3-oxobutanedioateHCID 80077AcetoacetamideHCID 517045Sodium Acetate

Product 1

HCID 13752508Diethyl 5-acetyl-1,6-dihydro-6-oxo-2,3-pyridinedicarboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium acetate (30 g, 0.37 mol) is added to a stirred mixture of diethyl(ethoxymethylene)oxalacetate (87 g, 0.36 mol) and acetoacetamide (36 g, 0.36 mol) in absolute ethanol (300 mL). After stirring the reaction mixture for 30 minutes, the ethanol is distilled off under reduced pressure, the residue acidified to pH 2 with dilute aqueous hydrochloric acid and the resulting solid filtered off. Crystallization from an ethanol-water mixture affords diethyl 5-acetyl-1,6-dihydro-6-oxo-2,3-pyridinedicarboxylate as crystals mp 101°-110° C.

Workup

  1. distillationthe ethanol is distilled off under reduced pressure
  2. filtrationthe resulting solid filtered off
  3. customCrystallization from an ethanol-water mixture

Sources & evidence

ORD record
ord-67167e46f9a6499bb42ca20c42085958
Source dataset
uspto-grants-1990_04
Patent number
US04920226

Reaction notes

Loading…