Allyl iodide → 7-(Methyloxy)-1-(2-propen-1-yl)-2(1H)-quinolinone

HRID 657002Notes

Reaction equation

HRID 657002 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9](=[O:13])[NH:10]2)=[CH:5][CH:4]=1.[H-].[Na+].[CH2:16](I)[CH:17]=[CH2:18]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9](=[O:13])[N:10]2[CH2:18][CH:17]=[CH2:16])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 11166Allyl iodideHCID 24758Sodium hydrideHCID 299427567-Methoxy-1,2-dihydroquinolin-2-one

Product 1

HCID 688097807-(Methyloxy)-1-(2-propen-1-yl)-2(1H)-quinolinone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 7-(methyloxy)-2(1H)-quinolinone (5 g, 0.029 mol) in DMF (70 ml) at 0° C. under N2 was added NaH (60% dispersion in oil; 2.5 g, 0.063 mol) stirred for 10 min, warmed to ambient temperature and stirred for a further 30 min. To this reaction mixture was added allyl iodide (3.13 ml, 0.034 mol) and stirred overnight. The reaction was quenched with water (20 ml) and concentrated. The product was obtained after column chromatography (gradient-5% MeOH in DCM) to yield 4.2 g (68%).

Workup

  1. stirringstirred for a further 30 min
  2. stirringstirred overnight
  3. customThe reaction was quenched with water (20 ml)
  4. concentrationconcentrated
  5. customThe product was obtained after column chromatography (gradient-5% MeOH in DCM)
  6. customto yield 4.2 g (68%)

Sources & evidence

ORD record
ord-2f84930bf6ef4be783b1c90a49e9ab38
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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