Dichloromethane → (7-Fluoro-2-oxo-1(2H)-quinolinyl)acetaldehyde

HRID 656858Notes

Reaction equation

HRID 656858 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH: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+].C(Cl)Cl>O1CCOCC1.O.O=[Os](=O)(=O)=O>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:15])[N:9]2[CH2:12][CH:13]=[O:17])=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 6344DichloromethaneHCID 23667635Sodium periodate3×HCID 688179827-Fluoro-1-(2-propen-1-yl)-2(1H)-quinolinone

Product 1

HCID 86635311(7-Fluoro-2-oxo-1(2H)-quinolinyl)acetaldehydeYield 88%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent3×HCID 312751,4-DioxaneSolvent

Procedure

A solution of 7-fluoro-1-(2-propen-1-yl)-2(1H)-quinolinone (0.909 g, 4.48 mmol) in 1,4-dioxane (50 ml) and water (30 ml) at 0° C. was treated with sodium periodate (2.20 g, 10.30 mmol) and OsO4 (4% in water, 5 ml). The reaction was warmed to rt and stirred at rt for 1 h before an extra 30 ml of water was added, after another 1 h more sodium periodate (2.20 g, 10.30 mmol) was added and after a further 2 h more sodium periodate (4.20 g, 19.70 mmol) was added. The reaction was then stirred at rt for 0.5 h before evaporation, treatment with water and extraction with DCM (×3). The combined organics were dried and evaporated to give the desired product (0.50 g, 88%). This material contained approximately 10% of the isomeric (5-fluoro-2-oxo-1(2H)-quinolinyl)acetaldehyde.

Workup

  1. additionwas added
  2. customThe combined organics were dried
  3. customevaporated

Sources & evidence

ORD record
ord-f93d5751a45f49778ec136c1d63757ed
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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