Sodium Hydroxide → 2-Chloro-6-fluoroquinoline

HRID 860023Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 860023
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=O)[CH:6]=[CH:5]2.P(Cl)(Cl)([Cl:15])=O.[OH-].[Na+]>C1(C)C=CC=CC=1>[Cl:15][C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([F:1])[CH:3]=2)[N:8]=1

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 98340436-Fluoro-1,2-dihydroquinolin-2-one

Produkt 1

HCID 150594332-Chloro-6-fluoroquinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

A mixture of 6-fluoroquinolin-2(1H)-one from Step C, (0.971 g, 6 mmol), phosphorous oxychloride (2.83 mL, 30 mmol), and toluene (20 mL) is heated at 95° C. for 2 hours. The reaction is cooled in an ice bath and basified with 50% aqueous sodium hydroxide. The mixture is extracted with ethyl acetate and the extracts are dried over anhydrous magnesium sulfate, filtered, and concentrated to an orange solid (1.01 g). The residue is flash chromatographed on silica gel Merck-60 with 5% ethyl acetate in hexane to provide the title compound as a light pink solid, m.p. 99–101° C.

Aufarbeitung

  1. temperatureThe reaction is cooled in an ice bath
  2. extractionThe mixture is extracted with ethyl acetate
  3. dry with materialthe extracts are dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to an orange solid (1.01 g)
  6. customchromatographed on silica gel Merck-60 with 5% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-db4f91d21adc4a57b597d344b7604f66
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07153849B2

Notizen zur Reaktion

Wird geladen…