Methyl iodide → 8-methoxy-1-methyl-3,4-dihydro-1H-quinolin-2-one

HRID 1811394Notes

Reaction equation

HRID 1811394 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[NH:11][C:10](=[O:13])[CH2:9][CH2:8]2.[H-].[Na+].[H][H].[CH3:18]I>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]([CH3:18])[C:10](=[O:13])[CH2:9][CH2:8]2

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 133754763,4-Dihydro-8-methoxy-2(1H)-quinolinoneHCID 178418361HCID 178418361, compound

Product 1

HCID 133841968-methoxy-1-methyl-3,4-dihydro-1H-quinolin-2-oneYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

8-Methoxy-3,4-dihydro-1H-quinolin-2-one (15 g) was dissolved in DMF (150 ml), and 3.6 g of sodium hydride (60% in oil) was added under ice cooling. After the addition, stirring was carried out at room temperature until the generation of hydrogen stopped. The resulting mixture was cooled with ice water again, and 5.8 ml of methyl iodide was added dropwise, followed by stirring at room temperature overnight. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to thereby obtain 16.7 g (yield: 96%) of 8-methoxy-1-methyl-3,4-dihydro-1H-quinolin-2-one.

Workup

  1. additionAfter the addition
  2. stirringby stirring at room temperature overnight
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-96f527c4a0e8489b880b21cbe161553e
Source dataset
uspto-grants-2013_01
Patent number
US08362252B2

Reaction notes

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