Sodium Methoxide → 7-Methoxy-1,8-naphthyridin-2(1H)-one

HRID 1801447Notes

Reaction equation

HRID 1801447 reaction equation
Cl[C:2]1[N:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1.[CH3:13][O-:14].[Na+]>CO>[CH3:13][O:14][C:2]1[N:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 133023227-Chloro-1,8-naphthyridin-2-ol

Product 1

HCID 217930287-Methoxy-1,8-naphthyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 7-chloro-1H-[1,8]naphthyridin-2-one (prepared as described in J. Org. Chem. (1990), 55, 4744; 5.36 g, 29.68 mmol) in MeOH (98 mL) was added sodium methoxide (25 wt % in MeOH, 161 mL). The resulting solution was stirred at reflux for 15 h. The solvent was removed in vacuo. Water (100 mL) and EA (80 mL) were added. The phases were separated and the aq layer was extracted with EA (8×80 mL). The combined org. layers were washed with brine (50 mL), dried over MgSO4, filtered and evaporated under reduced pressure. The title compound was obtained as a beige solid (5.22 g, 100% yield).

Workup

  1. temperatureat reflux for 15 h
  2. customThe solvent was removed in vacuo
  3. additionWater (100 mL) and EA (80 mL) were added
  4. customThe phases were separated
  5. extractionthe aq layer was extracted with EA (8×80 mL)
  6. washlayers were washed with brine (50 mL)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-d026cfd2f7a74e51a43c754ed138f90a
Source dataset
uspto-grants-2013_01
Patent number
US08349829B2

Reaction notes

Loading…