Methyl iodide → 7-Fluoro-4-(methyloxy)-1-(2-propen-1-yl)-2(1H)-quinolinone

HRID 657123Notes

Reaction equation

HRID 657123 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:16])=[CH:7][C:8](=[O:15])[N:9]2[CH2:12][CH:13]=[CH2:14])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:19]I>CN(C=O)C>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O:16][CH3:19])=[CH:7][C:8](=[O:15])[N:9]2[CH2:12][CH:13]=[CH2:14])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 688207057-Fluoro-4-hydroxy-1-(2-propen-1-yl)-2(1H)-quinolinone

Product 1

HCID 688164837-Fluoro-4-(methyloxy)-1-(2-propen-1-yl)-2(1H)-quinolinoneYield 36%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-fluoro-4-hydroxy-1-(2-propen-1-yl)-2(1H)-quinolinone (see Example 130(c) for a preparation) (1.0 g, 4.56 mmol) in DMF (50 ml) at 0° C. was added sodium hydride (0.20 g, 5.0 mmol, 60% in paraffin). To the resulting solution was added methyl iodide (0.3 ml, 4.8 mmol) and stirring continued at 0° C. for 1 h, then at ambient for 18 h. The mixture was evaporated and the residues separated between dichloromethane and water. The organics were isolated, dried and concentrated. Chromatography over silica (50 g SPE, eluting with dichloromethane) provided the title compound (0.386 g, 36%).

Workup

  1. waitat ambient for 18 h
  2. customThe mixture was evaporated
  3. customthe residues separated between dichloromethane and water
  4. customThe organics were isolated
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c00a4a28baaf4b92a56cc91a8c863b2a
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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