Dimethyl Sulfate → 4-Methoxy-1H-quinolin-2-one

HRID 896357Notes

Reaction equation

HRID 896357 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([OH:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[C:13](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>CC(C)=O>[CH3:13][O:12][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3][C:2](=[O:1])[CH:11]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 1785165532-hydroxy-1H-quinolin-4-one

Product 1

HCID 6001674-Methoxy-1H-quinolin-2-oneYield 54%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a suspension of 2,4-dihydroxy quinoline (3.00 g, 18.6 mmol) and potassium carbonate (5.14 g, 37.2 mmol) in acetone (500 mL) was added dimethyl sulfate (2.1 mL, 22 mmol) and the resulting mixture heated at reflux during 5 hrs. The solvent was removed in vacuo and the residue triturated in water. The product was collected by filtration, washed with water and triturated from methanol to give 4-methoxy 2-quinolone (1.76 g, 54%) as a white solid, that had identical 1H NMR data as reported (Reisch et al., Arch. Pharm., 1980, 313, 751-755). 3-(2,2,2-Trifluoro-ethyl)-1H-quinazoline-2,4-dione

Workup

  1. temperaturethe resulting mixture heated
  2. temperatureat reflux during 5 hrs
  3. customThe solvent was removed in vacuo
  4. customthe residue triturated in water
  5. filtrationThe product was collected by filtration
  6. washwashed with water
  7. customtriturated from methanol

Sources & evidence

ORD record
ord-044cf7a0e32a4857bf971eadda2bd2da
Source dataset
uspto-grants-2005_07
Patent number
US06919331B2

Reaction notes

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