Potassium Fluoride → 2-Fluoroquinoline-4-carboxylic acid methyl ester

HRID 47427

Reaktionsgleichung

Reaktionsgleichung von HRID 47427
[CH3:1][O:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[C:7](Cl)[CH:6]=1)=[O:4].[F-:16].[K+]>CS(C)(=O)=O.ClCCl.O>[CH3:1][O:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[C:7]([F:16])[CH:6]=1)=[O:4]

Komponenten

5

Edukt 2

HCID 522689Potassium FluorideHCID 5202936Methyl 2-chloroquinoline-4-carboxylate

Produkt 1

HCID 539678632-Fluoroquinoline-4-carboxylic acid methyl esterAusbeute 66,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6213Dimethyl SulfoneLösungsmittelHCID 21908982Water methylene chlorideLösungsmittel

Reaktionsbedingungen

Temperatur
180 °C

Versuchsvorschrift

2-Chloroquinoline-4-carboxylic acid methyl ester (1.14 g) in dimethylsulfone (4.0 g) was treated with potassium fluoride (2.5 g) and heated at 180° C. for 1 h. The reaction mixture was cooled to room temperature, diluted with dichloromethane:water (1:1, 200 ml), the organic phase separated, solvent removed at reduced pressure and the residue column chromatographed (silica gel, dichloromethane eluant) to give 2-fluoroquinoline-4-carboxylic acid methyl ester (0.7 g). 1H NMR (CDCl3) δ: 3.99 (3H, s), 7.57 (2H, m), 7.72 (1H, m), 7.95 (1H, d, J=8.5 Hz), 8.67 (1H, d, J=8.4 Hz). m/z (API+): 205 (MH+).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe organic phase separated
  3. customsolvent removed at reduced pressure
  4. customthe residue column chromatographed (silica gel, dichloromethane eluant)

Quellen und Nachweise

ORD-Eintrag
ord-c5db79bf0d3148d9bbb0dabc02bceb6e
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06699879B1

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