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

HRID 365086

Reaktionsgleichung

Reaktionsgleichung von HRID 365086
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-9f0cbae41001496fa03e54be8b0c05fb
Quelldatensatz
uspto-grants-1986_08
Patentnummer
US04608079

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