Potassium Iodide → HCID 22416860, compound

HRID 1721173Notes

Reaction equation

HRID 1721173 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH2:12][O:13][C:14]1[CH:15]=[C:16]([N+:20]([O-])=O)[CH:17]=[CH:18][CH:19]=1)[CH:8]=[CH:7]2.[N+]([C:26]1C=[C:28]([OH:32])[CH:29]=[CH:30][CH:31]=1)([O-])=O.BrC[C:35]1[CH:44]=CC2C(=C(F)C=CC=2)N=1.[C:46](=O)([O-:48])[O-:47].[K+].[K+].[I-].[K+]>CC(CC)=O>[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([CH2:12][O:13][C:14]1[CH:15]=[C:16]([NH:20][C:28](=[O:32])[CH2:29][C:30]([CH2:31][CH3:26])([CH2:44][CH3:35])[C:46]([OH:48])=[O:47])[CH:17]=[CH:18][CH:19]=1)[CH:8]=[CH:7]2

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 111373-NitrophenolHCID 11430Potassium CarbonateHCID 224168662-(Bromomethyl)-8-fluoroquinolineHCID 22416913HCID 22416913, compound

Product 1

HCID 22416860HCID 22416860, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

3-(8-fluoro-2-quinolinylmethoxy)nitrobenzene: 0.67 g of 3-nitrophenol and 1.15 g of 2-bromomethyl-8-fluoroquinoline are dissolved in 110 ml of ethyl methyl ketone; 3.3 g of potassium carbonate and 0.8 g of potassium iodide are added and the batch is heated under reflux for 3 hours. After cooling, removing the solid by filtration and evaporating the solvent in vacuo, 100 ml of dichloromethane are added to the residue, the batch is washed with water (twice, 20 ml each time), dried over sodium sulfate, filtered and freed of the solvent in vacuo to give the title compound in the form of pale yellow crystals of m.p. 128°-129° after recrystallisation from dichloromethane/hexane.

Workup

  1. temperaturethe batch is heated
  2. temperatureunder reflux for 3 hours
  3. temperatureAfter cooling
  4. customremoving the solid
  5. filtrationby filtration
  6. customevaporating the solvent in vacuo, 100 ml of dichloromethane
  7. additionare added to the residue
  8. washthe batch is washed with water (twice, 20 ml each time),
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered

Sources & evidence

ORD record
ord-f94ed679bd7a44429ad0cfb2e4cb3bd9
Source dataset
uspto-grants-1996_04
Patent number
US05508408

Reaction notes

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