Water → 7-Fluoro-1-(2-propen-1-yl)-2(1H)-quinolinone

HRID 656857Notes

Reaction equation

HRID 656857 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1.[H-].[Na+].[CH2:15](I)[CH:16]=[CH2:17].O>CN(C=O)C>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:12])[N:9]2[CH2:17][CH:16]=[CH2:15])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11166Allyl iodideHCID 24758Sodium hydrideHCID 190675757-Fluoroquinolin-2(1H)-one

Product 1

HCID 688179827-Fluoro-1-(2-propen-1-yl)-2(1H)-quinolinoneYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 7-fluoro-2(1H)-quinolinone (1.53 g, 9.39 mmol) in DMF at 0° C. was added sodium hydride (0.83 g of a 60% w:w dispersion in oil, 20.65 mmol) and the reaction was allowed warm to rt over 0.5 h before addition of allyl iodide (1.91 ml, 20.65 mmol). The reaction was stirred at rt for a further 0.25 h before addition of water (100 ml). The aqueous phase was then extracted with 10% MeOH in DCM (3×200 ml) and the combined organic phases were dried, evaporated and the residue was subjected to column chromatography on silica gel using a 10% MeOH in DCM gradient to provide the desired compound (0.91 g, 48%). This material contained approximately 10% of the isomeric 5-fluoro-1-(2-propen-1-yl)-2(1H)-quinolinone.

Workup

  1. extractionThe aqueous phase was then extracted with 10% MeOH in DCM (3×200 ml)
  2. customthe combined organic phases were dried
  3. customevaporated

Sources & evidence

ORD record
ord-e13544c094d04a578625721d7a513337
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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