Allyl iodide → 6,7-Difluoro-1-(2-propen-1-yl)-2(1H)-quinoxalinone

HRID 656981Notes

Reaction equation

HRID 656981 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[NH:8][C:7](=[O:13])[CH:6]=[N:5]2.C(=O)([O-])[O-].[K+].[K+].[CH2:20](I)[CH:21]=[CH2:22]>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[N:8]([CH2:22][CH:21]=[CH2:20])[C:7](=[O:13])[CH:6]=[N:5]2

Participants

5

Reactant 3

HCID 11166Allyl iodideHCID 11430Potassium CarbonateHCID 63243396,7-Difluoro-1,2-dihydroquinoxalin-2-one

Product 1

HCID 567924086,7-Difluoro-1-(2-propen-1-yl)-2(1H)-quinoxalinoneYield 63.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6,7-difluoro-2(1H)-quinoxalinone (0.57 g; 3.13 mmol) in dry DMF (10 ml) containing anhydrous potassium carbonate (1.3 g; 9.4 mmol) was treated with allyl iodide (0.31 ml; 3.45 mmol) and the mixture was stirred at rt for 2 h. The solvents were evaporated, water was added and the mixture was extracted (3×) with DCM. The extracts were dried and evaporated, and the residue was chromatographed on silica gel, eluting with 0-50% ethyl acetate/hexane to give the product (0.44 g, 63%).

Workup

  1. customThe solvents were evaporated
  2. additionwater was added
  3. extractionthe mixture was extracted (3×) with DCM
  4. customThe extracts were dried
  5. customevaporated
  6. customthe residue was chromatographed on silica gel
  7. washeluting with 0-50% ethyl acetate/hexane

Sources & evidence

ORD record
ord-c8f98b2d4d614475a9b34407c8721d59
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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