Potassium Carbonate → HCID 66917267, compound

HRID 2167466Notes

Reaction equation

HRID 2167466 reaction equation
C(=O)([O-])[O-].[K+].[K+].[I-:7].[F:8][C:9]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH3:22])=[C:15]2[C:10]=1[C:11](=[O:27])[CH:12]=[C:13]([C:23]([F:26])([F:25])[F:24])[NH:14]2.S([O-])([O-])=O.[Na+].[Na+]>C(OCC)(=O)C.CN(C=O)C>[F:8][C:9]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH3:22])=[C:15]2[C:10]=1[C:11](=[O:27])[C:12]([I:7])=[C:13]([C:23]([F:25])([F:26])[F:24])[NH:14]2

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 24437Sodium SulfiteHCID 30165Iodide IonHCID 66917197HCID 66917197, compound

Product 1

HCID 66917267HCID 66917267, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Potassium carbonate (3.73 g, 27 mmol) and iodide (6.85 g, 27 mmol) were added to a DMF solution (20 ml) of 5-fluoro-8-propoxy-2-trifluoromethyl-1H-quinolin-4-one (6.0 g, 20.7 mmol) in that order, and the resulting mixture was stirred at room temperature for 1.5 hours. A saturated sodium sulfite aqueous solution (20 ml) and ethyl acetate were added to the reaction mixture, and the precipitated solid was collected by filtration. The filtrate was washed with water, and then dried over anhydrous sodium sulfate. The dried filtrate was concentrated under reduced pressure. The residue and the substance collected by the advance filtration were combined, and dissolved in ethanol, and then concentrated. The residue was recrystallized from an ethyl acetate-n-hexane mixed solvent to thereby obtain 4.7 g of powdery white 5-fluoro-3-iodo-8-propoxy-2-trifluoromethyl-1H-quinolin-4-one (yield: 55%).

Workup

  1. filtrationthe precipitated solid was collected by filtration
  2. washThe filtrate was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationThe dried filtrate was concentrated under reduced pressure
  5. filtrationThe residue and the substance collected by the advance filtration
  6. dissolutiondissolved in ethanol
  7. concentrationconcentrated
  8. customThe residue was recrystallized from an ethyl acetate-n-hexane mixed solvent

Sources & evidence

ORD record
ord-725bd00f34484a469c0004e4ead36e83
Source dataset
uspto-grants-2015_06
Patent number
US09045464B2

Reaction notes

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