Iodoethane → 1-Chloro-7-fluoro-4-ethoxyisoquinoline

HRID 1852222Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1852222
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([F:12])[CH:10]=2)[C:5]([OH:13])=[CH:4][N:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:20](I)[CH3:21]>C(#N)C>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([F:12])[CH:10]=2)[C:5]([O:13][CH2:20][CH3:21])=[CH:4][N:3]=1

Komponenten

5

Edukt 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 717427161-Chloro-7-fluoroisoquinolin-4-OL

Produkt 1

HCID 866832671-Chloro-7-fluoro-4-ethoxyisoquinolineAusbeute 70,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of 1-chloro-7-fluoroisoquinolin-4-ol (0.5 g, 2.53 mmol) in acetonitrile (10 ml) was added K2CO3 (700 mg, 5.06 mmol) followed by ethyl iodide (475 mg, 3.04 mmol) at room temperature. The reaction mixture was stirred at room temperature for overnight. The solvent was evaporated under reduced pressure and the residue was diluted with water and extracted with ethyl acetate. The combined organic layer was dried over anhydrous Na2SO4 and evaporated under reduced pressure to get crude compound. The crude compound was purified by silica gel chromatography to get 1-chloro-7-fluoro-4-ethoxyisoquinoline (400 mg 70%) as off-white solid.

Aufarbeitung

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe residue was diluted with water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  5. customevaporated under reduced pressure
  6. customto get crude compound
  7. customThe crude compound was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7a9115e8fdb0409d93bf4d00ba942886
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08957203B2

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