Sodium Hydroxide → 6-Bromo4-(3-ethoxy-phenyl)-2-methoxy-quinoline

HRID 1936296Notes

Reaction equation

HRID 1936296 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH:6]=[C:5]2[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:20][CH3:21])[CH:14]=1.F[B-](F)(F)F.[CH3:27][O+](C)C.[OH-].[Na+]>ClC(Cl)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([O:12][CH3:27])[CH:6]=[C:5]2[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:20][CH3:21])[CH:14]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 224654436-Bromo4-(3-ethoxy-phenyl)-1h-quinolin-2-one

Product 1

HCID 224654196-Bromo4-(3-ethoxy-phenyl)-2-methoxy-quinolineYield 58.2%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a suspension of 6-bromo-4-(3-ethoxy-phenyl)-1H-quinolin-2-one (7.4 g, 21.5 mmol) in 60 ml dichloroethane was added trimethyloxonium tetrafluoroborate (BF4OMe3, 3.66 g, 24.7 mmol). The resulting mixture was stirred at ambient temperature overnight. After cooling to 0 C, was added 60 ml of 10% aqueous NaOH dropwise. The reaction mixture was stirred for another six hours at ambient temperature. It was then partitioned between dichloromethane and water. The organic layer was washed brine, dried over MgSO4, filtered and concentrated under vacuum to give an off-white solid. The solid was chromatographed on flash silica gel eluting with dichoromethane to yield the titled compound of 23A as a white solid (4.48 g, 58% yield).

Workup

  1. temperatureAfter cooling to 0 C
  2. stirringThe reaction mixture was stirred for another six hours at ambient temperature
  3. customIt was then partitioned between dichloromethane and water
  4. washThe organic layer was washed brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customto give an off-white solid
  9. customThe solid was chromatographed on flash silica gel eluting with dichoromethane

Sources & evidence

ORD record
ord-a18ddb22c6ce4e2b86855021b9f17ed9
Source dataset
uspto-grants-2002_05
Patent number
US06388092B2

Reaction notes

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