Water → 4-Methoxy-3-(2-methylphenyl)quinolin-2(1H)-one

HRID 364924Notes

Reaction equation

HRID 364924 reaction equation
Cl[C:2]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:20][O-:21].[Na+].[OH2:23]>CN(C)C=O>[CH3:20][O:21][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3][C:2](=[O:23])[C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:18]

Participants

5

Reactant 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 140012152,4-Dichloro-3-(2-methylphenyl)quinoline

Product 1

HCID 140012194-Methoxy-3-(2-methylphenyl)quinolin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2,4-dichloro-3-o-tolylquinoline (3 g.) and sodium methoxide (1.9 g.) in dimethylformamide (30 ml.) was heated at 60° for 6 hr. The mixture was cooled and poured into water (500 ml.), and the mixture was extracted with ethyl acetate (2×100 ml.). The ethyl acetate extract was washed with water (2×50 ml.) and then dried (MgSO4). The solvent was evaporated and the residue (containing 2,4-dimethoxy-3-o-tolylquinoline) was used without further purification. A mixture of said residue (2.6 g.) and 2M-hydrochloric acid (50 ml.) was heated at 100° for 2 hr. The mixture was cooled and filtered. The solid residue was crystallised from ethyl acetate-petroleum ether (b.p. 60°-80°) to give 4-methoxy-3-o-tolylquinolin-2-one, m.p. 215°.

Workup

  1. temperaturewas heated at 60° for 6 hr
  2. temperatureThe mixture was cooled
  3. extractionthe mixture was extracted with ethyl acetate (2×100 ml.)
  4. extractionThe ethyl acetate extract
  5. washwas washed with water (2×50 ml.)
  6. dry with materialdried (MgSO4)
  7. customThe solvent was evaporated
  8. additionthe residue (containing 2,4-dimethoxy-3-o-tolylquinoline)
  9. customwas used without further purification
  10. additionA mixture of said residue (2.6 g.) and 2M-hydrochloric acid (50 ml.)
  11. temperaturewas heated at 100° for 2 hr
  12. temperatureThe mixture was cooled
  13. filtrationfiltered
  14. customThe solid residue was crystallised from ethyl acetate-petroleum ether (b.p. 60°-80°)

Sources & evidence

ORD record
ord-50468eb0be3a4c3d8ee9feb4850eda29
Source dataset
uspto-grants-1986_08
Patent number
US04607039

Reaction notes

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