Methyl iodide → 5,6,7,8-tetrahydro-5-oxo-1,7,7-trimethyl-2(1H)-quinolinone

HRID 1033524Notes

Reaction equation

HRID 1033524 reaction equation
[CH3:1][C:2]1([CH3:14])[CH2:11][C:10]2[NH:9][C:8](=[O:12])[CH:7]=[CH:6][C:5]=2[C:4](=[O:13])[CH2:3]1.CI.[C:17](=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[O:13]=[C:4]1[CH2:3][C:2]([CH3:14])([CH3:1])[CH2:11][C:10]2[N:9]([CH3:17])[C:8](=[O:12])[CH:7]=[CH:6][C:5]1=2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 135163797,7-dimethyl-7,8-dihydroquinoline-2,5(1H,6H)-dione

Product 1

HCID 190261755,6,7,8-tetrahydro-5-oxo-1,7,7-trimethyl-2(1H)-quinolinoneYield 50.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5,6,7,8-tetrahydro-7,7-dimethyl-5-oxo-2(1H)-quinolinone (15.0 g), methyl iodide (12.3 g), potassium carbonate (21.6 g), and dimethylformamide (230 ml) was stirred at room temperature for 21 hrs. The reaction mixture was filtered, and the filtrate was concentrated. Ethyl acetate was added to the residue, and the mixture was filtered. The filtrate was washed with brine, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated to give 8.1 g (50%) of 5,6,7,8-tetrahydro-5-oxo-1,7,7-trimethyl-2(1H)-quinolinone.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. additionEthyl acetate was added to the residue
  4. filtrationthe mixture was filtered
  5. washThe filtrate was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-f762b8a0de354c83bf7f2af6580bb233
Source dataset
uspto-grants-1994_05
Patent number
US05310914

Reaction notes

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