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

HRID 385596Notes

Reaction equation

HRID 385596 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-c53baec6fd2e4cd5a5808caaf5ea6581
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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