Water → HCID 18776682, 화합물

HRID 55090노트

반응식

HRID 55090 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 18776682HCID 18776682, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

4-Nitrophenol (41 moles, 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 moles, 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.

후처리

  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

출처 및 근거

ORD 기록
ord-fed243506baa4837a73704b40237b86f
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05624937

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