Allyl iodide → 7-fluoro-1-(2-propen-1-yl)-2(1H)-quinoxalinone

HRID 656941

Reaktionsgleichung

Reaktionsgleichung von HRID 656941
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[CH:7][C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1.F[C:14]1[CH:15]=C2C(=C[CH:23]=1)NC(=O)C=N2.C(=O)([O-])[O-].[K+].[K+].C(I)C=C>CN(C=O)C>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[CH:7][C:8](=[O:12])[N:9]2[CH2:15][CH:14]=[CH2:23])=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 11166Allyl iodideHCID 11430Potassium CarbonateHCID 126863866-Fluoro-1,2-dihydroquinoxalin-2-oneHCID 217275347-fluoroquinoxalin-2(1H)-one

Produkt 1

HCID 688167377-fluoro-1-(2-propen-1-yl)-2(1H)-quinoxalinone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A 1:2 mixture of 7-fluoro-2(1H)-quinoxalinone and 6-fluoro-2(1H)-quinoxalinone (20 g, 0.122 mol) in dry DMF (250 ml) and anhydrous potassium carbonate (50.5 g, 0.38 mol) was treated with allyl iodide (12.3 ml, 0.134 mol) and the mixture was stirred at rt for 2 hours. The reaction mixture was evaporated to dryness, water was added and the mixture was extracted (3×) with DCM, washed with water, dried (sodium sulphate) and evaporated. It was chromatographed, twice, on silica gel, eluting with 0-40% ethyl acetate-hexane. The early fractions gave 7-fluoro-1-(2-propen-1-yl)-2(1H)-quinoxalinone (4.7 g) [later fractions contained the isomeric 6-fluoro-isomer (6.7 g)].

Aufarbeitung

  1. customThe reaction mixture was evaporated to dryness, water
  2. additionwas added
  3. extractionthe mixture was extracted (3×) with DCM
  4. washwashed with water
  5. dry with materialdried (sodium sulphate)
  6. customevaporated
  7. customIt was chromatographed
  8. washtwice, on silica gel, eluting with 0-40% ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-4552e6b93cb24edeb2e5d73173959c23
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071592B2

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