Sodium periodate → (7-methoxy-2-oxoquinolin-1(2H)-yl)acetaldehyde

HRID 657003Notes

Reaction equation

HRID 657003 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9](=[O:16])[N:10]2[CH2:13][CH:14]=C)=[CH:5][CH:4]=1.I([O-])(=O)(=O)=[O:18].[Na+]>O1CCOCC1.O.[Os](=O)(=O)(=O)=O>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9](=[O:16])[N:10]2[CH2:13][CH:14]=[O:18])=[CH:5][CH:4]=1

Participants

6

Reactant 2

HCID 23667635Sodium periodateHCID 68809780HCID 68809780, compound

Product 1

HCID 59397833(7-methoxy-2-oxoquinolin-1(2H)-yl)acetaldehydeYield 71%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 7-(methyloxy)-1-(2-propen-1-yl)-2(1H)-quinolinone (4.14 g, 0.019 mol) in 1,4-dioxane (80 ml) and water (40 ml) under N2 was added sodium periodate (9.5 g; 0.044 mol) and osmium tetroxide (10 ml, 4% aqueous solution) and stirred overnight. The reaction was concentrated and partitioned in 20% MeOH/DCM (300 ml) and water (200 ml). The organic layer was dried over magnesium sulphate, filtered, and concentrated. The product was obtained after column chromatography (neat ethyl acetate) to yield g (71%) of the title compound as a green solid.

Workup

  1. concentrationThe reaction was concentrated
  2. custompartitioned in 20% MeOH/DCM (300 ml)
  3. dry with materialThe organic layer was dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe product was obtained after column chromatography (neat ethyl acetate)

Sources & evidence

ORD record
ord-f361fc962ee64c8ab2923ca82377251c
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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