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

HRID 256124

Reaktionsgleichung

Reaktionsgleichung von HRID 256124
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]

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

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 200°-209° C.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-11ec135ee81b486d86692e51990b1186
Quelldatensatz
uspto-grants-1987_10
Patentnummer
US04701208

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