Methyl iodide → 5-[2-(2-Chloro-5-methoxy-phenyl)-propionyl]-1-methyl-1H-pyridin-2-one
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH2:10][C:11]([C:13]1[CH:14]=[CH:15][C:16](=[O:20])[N:17]([CH3:19])[CH:18]=1)=[O:12].[H-].[Na+].CI.[C:25](OCC)(=O)C>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH:10]([CH3:25])[C:11]([C:13]1[CH:14]=[CH:15][C:16](=[O:20])[N:17]([CH3:19])[CH:18]=1)=[O:12]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
To a suspension of 5-[2-(2-chloro-5-methoxy-phenyl)-acetyl]-1-methyl-1H-pyridin-2-one (9.35 g) in tetrahydrofuran (110 ml) was added sodium hydride (60% dispersion in mineral oil, 1.35 g) in three portions. The mixture was stirred at 40° C. for 1 h and then placed in an ice bath. Methyl iodide (5.01 g) was added dropwise. The mixture was stirred at 0° C. for 10 min and at room temperature for 2 h. Ethyl acetate was added and the mixture was washed with water and brine. The organic phase was dried (MgSO4), filtered and concentrated to dryness. The residue was washed with cyclohexane, filtered and dried to give the title compound as an off-white solid (9.45 g). MS (m/e)=306.2 [M+H+].
Workup
- customplaced in an ice bath
- stirringThe mixture was stirred at 0° C. for 10 min and at room temperature for 2 h
- washthe mixture was washed with water and brine
- dry with materialThe organic phase was dried (MgSO4)
- filtrationfiltered
- concentrationconcentrated to dryness
- washThe residue was washed with cyclohexane
- filtrationfiltered
- customdried
Sources & evidence
- ORD record
- ord-310cf3280a8447438a37dd13dbcad494
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08138189B2
Reaction notes
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