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

HRID 656941Notes

Reaction equation

HRID 656941 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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)].

Workup

  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

Sources & evidence

ORD record
ord-4552e6b93cb24edeb2e5d73173959c23
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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