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Water → 1-(1,3-dioxolan-2-ylmethyl)-7-hydroxy-1,5-naphthyridin-2(1H)-one

HRID 1510717
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1510717
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][N:7]1[C:16]2[C:11](=[N:12][CH:13]=[C:14](F)[CH:15]=2)[CH:10]=[CH:9][C:8]1=[O:18].[OH-:19].[Na+].O>O1CCCC1>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][N:7]1[C:16]2[C:11](=[N:12][CH:13]=[C:14]([OH:19])[CH:15]=2)[CH:10]=[CH:9][C:8]1=[O:18]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 962WaterHCID 14798Sodium Hydroxide2×HCID 578152081-(1,3-dioxolan-2-ylmethyl)-7-fluoro-1,5-naphthyridin-2(1H)-one

Produkt 1

HCID 578153801-(1,3-dioxolan-2-ylmethyl)-7-hydroxy-1,5-naphthyridin-2(1H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a suspension of 0.50 g of 1-(1,3-dioxolan-2-ylmethyl)-7-fluoro-1,5-naphthyridin-2(1H)-one in 3 mL of tetrahydrofuran, 3 mL of a 20% aqueous sodium hydroxide solution was added, and the mixture was heated under reflux while stirring for 1 hour. Thereto was added 3 mL of water, and the mixture was heated under reflux while stirring for 3 hours 30 minutes. Thereto was added 3 mL of a 20% aqueous sodium hydroxide solution, and the mixture was heated under reflux while stirring for 4 hours. Tetrahydrofuran was distilled off under reduced pressure, and the mixture was then heated under reflux while stirring for 1 hour 30 minutes. After cooling to room temperature, the reaction mixture was added with 2 mol/L hydrochloric acid and adjusted to pH 5. Thereto was added ethyl acetate, the organic layer was separated, and the aqueous layer was extracted twice with ethyl acetate. The organic layer and the extract were combined, the resultant solution was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. Diethyl ether was added to the resultant residue, and the solid was filtered off to obtain 0.32 g of 1-(1,3-dioxolan-2-ylmethyl)-7-hydroxy-1,5-naphthyridin-2(1H)-one as a yellow solid.

Aufarbeitung

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperatureunder reflux
  4. temperaturethe mixture was heated
  5. temperatureunder reflux
  6. stirringwhile stirring for 3 hours 30 minutes
  7. temperaturethe mixture was heated
  8. temperatureunder reflux
  9. stirringwhile stirring for 4 hours
  10. distillationTetrahydrofuran was distilled off under reduced pressure
  11. temperaturethe mixture was then heated
  12. temperatureunder reflux
  13. stirringwhile stirring for 1 hour 30 minutes
  14. additionthe reaction mixture was added with 2 mol/L hydrochloric acid
  15. additionThereto was added ethyl acetate
  16. customthe organic layer was separated
  17. extractionthe aqueous layer was extracted twice with ethyl acetate
  18. washthe resultant solution was washed with a saturated aqueous sodium chloride solution
  19. dry with materialdried over anhydrous magnesium sulfate
  20. distillationthe solvent was distilled off under reduced pressure
  21. additionDiethyl ether was added to the resultant residue
  22. filtrationthe solid was filtered off

Quellen und Nachweise

ORD-Eintrag
ord-30c767ad83b840f787c9065057dbdf60
Quelldatensatz
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08211908B2

Notizen zur Reaktion

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