Water → 5,7-Difluoro-1-(2-propen-1-yl)-2(1H)-quinolinone

HRID 656936Notes

Reaction equation

HRID 656936 reaction equation
[F:1][C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6](=[O:13])[NH:7]2.[H-].[Na+].[CH2:16](I)[CH:17]=[CH2:18].O>CN(C=O)C>[F:1][C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6](=[O:13])[N:7]2[CH2:18][CH:17]=[CH2:16]

Participants

6

Reactant 4

HCID 962WaterHCID 11166Allyl iodide2×HCID 24758Sodium hydride2×HCID 642082495,7-Difluoro-1,2-dihydroquinolin-2-one

Product 1

HCID 688160015,7-Difluoro-1-(2-propen-1-yl)-2(1H)-quinolinoneYield 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 5,7-difluoro-2(1H)-quinolinone (640 mg, 3.54 mmol) in DMF (15 ml) under argon at 0° C. was treated with sodium hydride (60% in mineral oil, 312 mg, 7.8 mmol) and then it was warmed up at rt. After 0.5 h at rt allyl iodide (0.72 mL, 7.8 mmol) was added. After 0.5 h sodium hydride (60% in mineral oil, 200 mg, 5 mmol) and allyl iodide (0.35 ml, 3.8 mmol) were added. Water (15 ml) was added and the aqueous was extracted using DCM (3×50 ml). The combined organic phases were dried, evaporated and the residue was chromatographed on silica gel, eluting with 0-4% MeOH-DCM to afford 350 mg of the desired compound (45%).

Workup

  1. extractionthe aqueous was extracted
  2. customThe combined organic phases were dried
  3. customevaporated
  4. customthe residue was chromatographed on silica gel
  5. washeluting with 0-4% MeOH-DCM

Sources & evidence

ORD record
ord-34f47e575e624c28a977781e0cb5ed46
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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