Chloroform → 4-(3-Fluoro-4-nitrophenoxy)-6-methoxy-7-(phenylmethoxy)quinoline

HRID 1008330노트

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HRID 1008330 반응식
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](Cl)=[CH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:22][C:23]1[CH:24]=[C:25]([OH:32])[CH:26]=[CH:27][C:28]=1[N+:29]([O-:31])=[O:30].C(Cl)(Cl)Cl.[OH-].[Na+]>ClC1C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:32][C:25]3[CH:26]=[CH:27][C:28]([N+:29]([O-:31])=[O:30])=[C:23]([F:22])[CH:24]=3)=[CH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 6212ChloroformHCID 14798Sodium HydroxideHCID 5209483-Fluoro-4-nitrophenolHCID 226465627-(Benzyloxy)-4-chloro-6-methoxyquinoline

생성물 1

HCID 226671344-(3-Fluoro-4-nitrophenoxy)-6-methoxy-7-(phenylmethoxy)quinoline수율 47%

시약·촉매·용매 1

HCID 7964Chlorobenzene용매

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온도
130 °C

실험 절차

7-(Benzyloxy)-4-chloro-6-methoxyquinoline (300 mg) and 3-fluoro-4-nitrophenol (785 mg) were dissolved in chlorobenzene (3 ml), and the solution was stirred at 130° C. for 5 hr. Chloroform and an aqueous sodium hydroxide solution were added to the reaction solution, and the mixture was stirred for one hr. The reaction solution was extracted with chloroform, and the chloroform layer was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was purified by thin-layer chromatography on silica gel by development with hexane/ethyl acetate (1/1) to give 197 mg (yield 47%) of the title compound.

후처리

  1. stirringthe mixture was stirred for one hr
  2. extractionThe reaction solution was extracted with chloroform
  3. dry with materialthe chloroform layer was dried over anhydrous magnesium sulfate
  4. customThe solvent was removed by distillation under the reduced pressure
  5. customThe residue was purified by thin-layer chromatography on silica gel by development with hexane/ethyl acetate (1/1)

출처 및 근거

ORD 기록
ord-063d369fc746484686519e5e9b796631
출처 데이터셋
uspto-grants-2004_09
특허 번호
US06797823B1

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