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

HRID 1962419Notes

Reaction equation

HRID 1962419 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 NaOMe (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-4cd23da051df43cdabbdb24cce5238bf
Source dataset
uspto-grants-2013_04
Patent number
US08415375B2

Reaction notes

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