Water → [7-Fluoro-4-(methyloxy)-2-oxo-1(2H)-quinolinyl]acetaldehyde

HRID 657124Notes

Reaction equation

HRID 657124 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O:16][CH3:17])=[CH:7][C:8](=[O:15])[N:9]2[CH2:12][CH:13]=C)=[CH:4][CH:3]=1.I([O-])(=O)(=O)=[O:19].[Na+].O>O1CCOCC1.[Os](=O)(=O)(=O)=O>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O:16][CH3:17])=[CH:7][C:8](=[O:15])[N:9]2[CH2:12][CH:13]=[O:19])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 23667635Sodium periodateHCID 688164837-Fluoro-4-(methyloxy)-1-(2-propen-1-yl)-2(1H)-quinolinone

Product 1

HCID 86635362[7-Fluoro-4-(methyloxy)-2-oxo-1(2H)-quinolinyl]acetaldehydeYield 93.2%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of 7-fluoro-4-(methyloxy)-1-(2-propen-1-yl)-2(1H)-quinolinone (0.386 g, 1.66 mmol), sodium periodate (0.83 g, 3.7 mmol) and osmium tetroxide (1.7 ml, 4% in water) in 1,4-dioxane (15 ml) containing water (3 ml) was stirred for 5 h. The mixture was separated between dichloromethane and water. The organics were isolated, dried and concentrated to provide the title compound (0.364 g, 93%).

Workup

  1. customThe mixture was separated between dichloromethane and water
  2. customThe organics were isolated
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4befbd37fc2546b69f661405ac5f9316
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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