Dimethylformamide → HCID 66596881, compound

HRID 504007Notes

Reaction equation

HRID 504007 reaction equation
[H-].[Na+].CN(C=O)C.[CH3:8][O:9][C:10]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:16]2[C:11]=1[CH2:12][CH2:13][C:14](=[O:26])[NH:15]2.Br[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[CH:31][CH:30]=1>C(OCC)(=O)C.O>[C:32]1([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:31]=[CH:30][C:29]([CH2:28][N:15]2[C:16]3[C:11](=[C:10]([O:9][CH3:8])[CH:19]=[CH:18][C:17]=3[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:12][CH2:13][C:14]2=[O:26])=[CH:34][CH:33]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 2577161,1'-Biphenyl, 4-(bromomethyl)-HCID 66596986HCID 66596986, compound

Product 1

HCID 66596881HCID 66596881, compoundYield 82.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (60% in oil) (0.87 g) was added at 0° C. to a DMF solution (50 ml) of 5-methoxy-8-phenyl-3,4-dihydro-1H-quinolin-2-one (5.0 g), followed by stirring for 30 minutes. 4-Bromomethylbiphenyl (5.37 g) was added, and the resulting mixture was stirred at room temperature for 1 hour. Water was added to the reaction mixture, and extraction with ethyl acetate was performed. The extract was washed with a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:10→1:5). The purified product was recrystallized from an ethyl acetate-n-hexane-diethyl ether mixed solvent to thereby obtain 6.8 g (yield: 82%) of 1-(biphenyl-4-ylmethyl)-5-methoxy-8-phenyl-3,4-dihydro-1H-quinolin-2-one as a white powder.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 1 hour
  2. washThe extract was washed with a saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:10→1:5)
  6. customThe purified product was recrystallized from an ethyl acetate-n-hexane-diethyl ether mixed solvent

Sources & evidence

ORD record
ord-c0b411bfeb7c43a395cfcc33f566f24f
Source dataset
uspto-grants-2010_08
Patent number
US07777038B2

Reaction notes

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