Potassium Iodide → HCID 24751745, Verbindung

HRID 1477456Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1477456
[F:1][C:2]1[CH:11]=[CH:10][C:9]([F:12])=[C:8]2[C:3]=1[C:4](=[O:18])[C:5]([C:13]([O:15]CC)=[O:14])=[CH:6][NH:7]2.[I-].[K+].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1>CN(C=O)C.O.C(OCC)(=O)C>[F:1][C:2]1[CH:11]=[CH:10][C:9]([F:12])=[C:8]2[C:3]=1[C:4](=[O:18])[C:5]([C:13]([OH:15])=[O:14])=[CH:6][N:7]2[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1

Komponenten

8

Edukt 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 2800571Ethyl 5,8-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

Produkt 1

HCID 24751745HCID 24751745, VerbindungAusbeute 64,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of ethyl 5,8-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate (5.0 g), potassium iodide (3.3 g) and potassium carbonate (4.1 g) in DMF (100 mL) was added 1-(chloromethyl)-4-methoxybenzene (4.6 g), and the mixture was stirred at 70° C. for 14 hr. The reaction mixture was diluted with water and ethyl acetate, and the organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated. The obtained residue was dissolved in ethanol-THF (1:1, 40 mL), 1 N aqueous sodium hydroxide solution (20 mL) was added, and the mixture was stirred at room temperature for 6 hr. The reaction mixture was diluted with water, neutralized with 1 N hydrochloric acid (20 mL), and the precipitate was collected by filtration, washed with water, and dried to give the title compound (4.4 g).

Aufarbeitung

  1. customthe organic layer was separated
  2. washwashed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. dissolutionThe obtained residue was dissolved in ethanol-THF (1:1, 40 mL)
  6. addition1 N aqueous sodium hydroxide solution (20 mL) was added
  7. stirringthe mixture was stirred at room temperature for 6 hr
  8. additionThe reaction mixture was diluted with water
  9. filtrationthe precipitate was collected by filtration
  10. washwashed with water
  11. customdried

Quellen und Nachweise

ORD-Eintrag
ord-17c682a6c00e472dbd3181f823903375
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09403802B2

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