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

HRID 1008330ノート

反応式

HRID 1008330 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 7964Chlorobenzene溶媒

反応条件

温度
130 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-063d369fc746484686519e5e9b796631
出典データセット
uspto-grants-2004_09
特許番号
US06797823B1

反応ノート

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