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Acetyl chloride → Ethyl 2-oxo-1,2-dihydropyridine-4-carboxylate

HRID 500535
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 500535
[C:1](Cl)(=[O:3])[CH3:2].[OH:5][C:6]1[CH:11]=[C:10]([C:12](O)=[O:13])[CH:9]=[CH:8][N:7]=1>C(O)C>[CH2:1]([O:3][C:12]([C:10]1[CH:9]=[CH:8][NH:7][C:6](=[O:5])[CH:11]=1)=[O:13])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 6367Acetyl chlorideHCID 178524562HCID 178524562, Verbindung

Produkt 1

HCID 22625086Ethyl 2-oxo-1,2-dihydropyridine-4-carboxylateAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Acetyl chloride (20 mL) was added slowly to ethanol (80 mL) at room temperature. The clear solution was stirred for 5 minutes and then 2-hydroxy-4-pyridinecarboxylic acid (5.0 g, 35.9 mmol) was added as a solid. The reaction mixture was heated at reflux overnight. The reaction mixture was cooled to room temperature and the majority of the ethanol was evaporated. The residue was diluted with chloroform and water and the aqueous layer was neutralized by the careful addition of K2CO3. The organic layer was separated and the aqueous layer was extracted further with chloroform. The combined organic layer was dried over sodium sulfate and concentrated to give the title compound (5.74 g, 96%).

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. customthe majority of the ethanol was evaporated
  4. additionThe residue was diluted with chloroform and water
  5. additionthe aqueous layer was neutralized by the careful addition of K2CO3
  6. customThe organic layer was separated
  7. extractionthe aqueous layer was extracted further with chloroform
  8. dry with materialThe combined organic layer was dried over sodium sulfate
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-df0492600fc6478aa95dd6a0cd3d3479
Quelldatensatz
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07772235B2

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