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Water → 1-(6-Methoxy-3-pyridinyl)-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylic acid

HRID 2194539
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2194539
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([N:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][N:17]=3)[CH:12]=[C:11]([C:19]([O:21]CC)=[O:20])[C:10]2=[O:24])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].O>O1CCOCC1>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([N:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][N:17]=3)[CH:12]=[C:11]([C:19]([OH:21])=[O:20])[C:10]2=[O:24])=[CH:5][CH:4]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 67010881Ethyl (6-methoxy-3-pyridinyl)-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate

Produkt 1

HCID 670096411-(6-Methoxy-3-pyridinyl)-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylic acidAusbeute 37,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31275
1,4-Dioxane
Lösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

4.1 g (13 mmol) of ethyl (6-methoxy-3-pyridinyl)-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate was dissolved in 1,4-dioxane (60 mL), and 2.6 g (19 mmol) of potassium carbonate and 100 mL of water were added thereto at room temperature. The resulting mixture was stirred for 3 hours at 60° C. The solvent was distilled off under reduced pressure from the reaction mixture, and the residue was dissolved in water and washed with chloroform. Concentrated hydrochloric acid was added to the aqueous phase to make the aqueous phase acidic, and the mixture was extracted with chloroform. The organic phase was dried and concentrated. Thus, 1.45 g of the title compound was obtained as colorless crystals (yield: 39%).

Aufarbeitung

  1. customat room temperature
  2. distillationThe solvent was distilled off under reduced pressure from the reaction mixture
  3. dissolutionthe residue was dissolved in water
  4. washwashed with chloroform
  5. additionConcentrated hydrochloric acid was added to the aqueous phase
  6. extractionthe mixture was extracted with chloroform
  7. customThe organic phase was dried
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-a6b0945fd71a46b283b32430e61ddbf4
Quelldatensatz
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08334236B2

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