Methyl iodide → 1,4-Dimethyl-7-(thiophen-3-yl)-1,2,5,6,7,8-hexahydroquinoline-2,5-dione

HRID 1700650Notes

Reaction equation

HRID 1700650 reaction equation
[CH3:1][C:2]1[C:11]2[C:10](=[O:12])[CH2:9][CH:8]([C:13]3[CH:17]=[CH:16][S:15][CH:14]=3)[CH2:7][C:6]=2[NH:5][C:4](=[O:18])[CH:3]=1.[H-].[Na+].[CH3:21]I>CN(C)C=O>[CH3:21][N:5]1[C:6]2[CH2:7][CH:8]([C:13]3[CH:17]=[CH:16][S:15][CH:14]=3)[CH2:9][C:10](=[O:12])[C:11]=2[C:2]([CH3:1])=[CH:3][C:4]1=[O:18]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 183175574-Methyl-7-(thiophen-3-yl)-1,2,5,6,7,8-hexahydroquinoline-2,5-dione

Product 1

HCID 183173001,4-Dimethyl-7-(thiophen-3-yl)-1,2,5,6,7,8-hexahydroquinoline-2,5-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-methyl-7-(thiophen-3-yl)-1,2,5,6,7,8-hexahydroquinoline-2,5-dione (0.518 g) in dimethylformamide (5 ml) was added at room temperature 60% sodium hydride (0.08 g) and then was added methyl iodide (0.3 ml), and the mixture was stirred at room temperature for 4 hours. Under reduced pressure, the solvent was evaporated, and the residue was extracted with ethyl acetate. The organic layer was washed with water and concentrated under reduced pressure. The resulting crystals were washed with ethyl acetate to give 1,4-dimethyl-7-(thiophen-3-yl)-1,2,5,6,7,8-hexahydroquinoline-2,5-dione (0.405 g) as colorless crystals.

Workup

  1. customUnder reduced pressure, the solvent was evaporated
  2. extractionthe residue was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. concentrationconcentrated under reduced pressure
  5. washThe resulting crystals were washed with ethyl acetate

Sources & evidence

ORD record
ord-6b66f805f92d4685b790fe838cc30ed7
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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