Sodium periodate → (7-fluoro-2-oxo-1(2H)-quinoxalinyl)acetaldehyde

HRID 656942Notes

Reaction equation

HRID 656942 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[CH:7][C:8](=[O:15])[N:9]2[CH2:12][CH:13]=C)=[CH:4][CH:3]=1.I([O-])(=O)(=O)=[O:17].[Na+]>O1CCOCC1.O.[Os](=O)(=O)(=O)=O>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[CH:7][C:8](=[O:15])[N:9]2[CH2:12][CH:13]=[O:17])=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 23667635Sodium periodateHCID 688167377-fluoro-1-(2-propen-1-yl)-2(1H)-quinoxalinone

Product 1

HCID 59397887(7-fluoro-2-oxo-1(2H)-quinoxalinyl)acetaldehyde

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 7-fluoro-1-(2-propen-1-yl)-2(1H)-quinoxalinone (2.4 g, 11.77 mmol) in 1,4-dioxane (140 ml) and water (250 ml) was treated with osmium tetroxide (4% solution in water; 14.5 ml) and sodium periodate (11.9 g) and the mixture was stirred at rt for 1.5 hours. It was evaporated to dryness onto silica gel and chromatographed on a 300 g silica gel column, eluting with 1:1 ethyl acetate-hexane then ethyl acetate. The early fractions gave (7-fluoro-2-oxo-1(2H)-quinoxalinyl)acetaldehyde which was triturated with ether/DCM 3:1 to give product (1.56 g).

Workup

  1. customIt was evaporated to dryness onto silica gel
  2. customchromatographed on a 300 g silica gel column
  3. washeluting with 1:1 ethyl acetate-hexane

Sources & evidence

ORD record
ord-2d013c7329774100a667f088b0b0cafd
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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