Water → HCID 18776682, compound

HRID 55090Notes

Reaction equation

HRID 55090 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

HCID 18776682HCID 18776682, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-fed243506baa4837a73704b40237b86f
Source dataset
uspto-grants-1997_04
Patent number
US05624937

Reaction notes

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