Water → HCID 18776682、化合物

HRID 2395346ノート

反応式

HRID 2395346 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].[H-].[Na+].Cl[C:14]1[CH:23]=[CH:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=1.O>CN(C=O)C>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

参加物

6

反応物 4

HCID 962WaterHCID 9804-NitrophenolHCID 119282-ChloroquinolineHCID 24758Sodium hydride

生成物 1

HCID 18776682HCID 18776682、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

4-Nitrophenol(41 mmoles, 5.1 g) was dissolved in DMF (500 ml) and treated with sodium hydride (41 mmoles previously washed with hexane). After stirring at room temperature for 1 hr, 2-chloroquinoline (40 mmoles, 6.5 g) was added dropwise and stirred for 16 hr at room temperature followed by refluxing for 6 hr. Water was added to the cooled solution and the product was extracted with ethyl acetate. The ethyl acetate solution was washed with water, and 5N NaOH, dried over sodium sulfate and concentrated. The product was purified by HPLC over silica gel eluted with ethyl acetate/hexane to yield 2-(4-nitrophenoxy)quinoline. 3.1 mmoles, 8%. Mass Spec (FD) 266. Calcd for C15H10N2O3 : C 67.45; H, 3.84; N, 10.40. Found: C, 65.84; H, 3.88; N, 8.47.

後処理

  1. washpreviously washed with hexane)
  2. stirringstirred for 16 hr at room temperature
  3. temperatureby refluxing for 6 hr
  4. extractionthe product was extracted with ethyl acetate
  5. washThe ethyl acetate solution was washed with water, and 5N NaOH
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customThe product was purified by HPLC over silica gel
  9. washeluted with ethyl acetate/hexane

出典と根拠

ORDレコード
ord-e06969149e21435ca43ec30706df22f7
出典データセット
uspto-grants-1998_09
特許番号
US05814646

反応ノート

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