Sodium hydride → 5-(2,4-Dimethylphenyl)-3-methyl-1-(1-propylbutyl)cinnolin-4(1H)-one
Reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[C:11](=[O:20])[C:12]([CH3:19])=[N:13][NH:14]2.Br[CH:22]([CH2:26][CH2:27][CH3:28])[CH2:23][CH2:24][CH3:25].[H-].[Na+]>CN1CCCC1>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[C:11](=[O:20])[C:12]([CH3:19])=[N:13][N:14]2[CH:22]([CH2:26][CH2:27][CH3:28])[CH2:23][CH2:24][CH3:25]Participants
5
Procedure
To 0.041 g (0.16 mmol) of 5-(2,4-dimethylphenyl)-3-methylcinnolin-4(1H)-one in 0.5 mL of N-methylpyrrolidine was added 0.069 mL of 4-bromoheptane and 0.012 g (0.31 mmol) of sodium hydride (60% dispersion in mineral oil). The mixture was stirred for 75 min. at room temperature and quenched with water. The mixture was extracted with ethyl acetate and the combined organics were washed with water and brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography eluting with a 8% ethyl acetate/hexanes mixture to give 0.042 g (75%) of the title compound as a light green-yellow semisolid.
Workup
- customquenched with water
- extractionThe mixture was extracted with ethyl acetate
- washthe combined organics were washed with water and brine
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by flash chromatography
- washeluting with a 8% ethyl acetate/hexanes mixture
Sources & evidence
- ORD record
- ord-4c6d66c81a604cbdb3c98764ce69fe95
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07897607B2
Reaction notes
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