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

HRID 50163

반응식

HRID 50163 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-8cb0a23cb9cb4214a6753163d2276bc8
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06710209B2

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