Acetonitrile → HCID 66596956, compound

HRID 1811424Notes

Reaction equation

HRID 1811424 reaction equation
Cl[CH2:2][C:3]1[CH:25]=[CH:24][C:6]([CH2:7][N:8]2[C:17]3[C:12](=[C:13]([CH:18]4[O:22][CH2:21][CH2:20][O:19]4)[CH:14]=[CH:15][CH:16]=3)[CH2:11][CH2:10][C:9]2=[O:23])=[CH:5][CH:4]=1.[CH3:26][NH:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(=O)([O-])[O-].[K+].[K+].C(#N)C>ClCCl.O>[O:19]1[CH2:20][CH2:21][O:22][CH:18]1[C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:12]=1[CH2:11][CH2:10][C:9](=[O:23])[N:8]2[CH2:7][C:6]1[CH:24]=[CH:25][C:3]([CH2:2][N:27]([CH3:26])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:4][CH:5]=1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 7515N-MethylanilineHCID 11430Potassium CarbonateHCID 66596909HCID 66596909, compound

Product 1

HCID 66596956HCID 66596956, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

1-(4-Chloromethylbenzyl)-5-(1,3-dioxolan-2-yl)-3,4-dihydro-1H-quinolin-2-one (100 mg, 0.28 mmol), N-methylaniline (0.045 ml, 0.42 mmol) and potassium carbonate (57.9 mg, 0.42 mmol) were added to acetonitrile (1 ml), followed by heating under reflux for 4 hours. After cooling to room temperature, water was added to the reaction mixture, and extraction with dichloromethane was performed. The organic layer was washed with water and a saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The dry product was concentrated under reduced pressure, and the residue was purified by preparative silica gel thin layer chromatography (n-hexane:ethyl acetate=1:1). The purified product was concentrated to dryness under reduced pressure to thereby obtain 80 mg (yield: 67%) of 5-(1,3-dioxolan-2-yl)-1-(4-[(N-methyl-N-phenylamino)methyl]benzyl)-3,4-dihydro-1H-quinolin-2-one as a light yellow amorphous solid.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 4 hours
  3. washThe organic layer was washed with water
  4. dry with materiala saturated sodium chloride solution, and dried over anhydrous sodium sulfate
  5. concentrationThe dry product was concentrated under reduced pressure
  6. customthe residue was purified by preparative silica gel thin layer chromatography (n-hexane:ethyl acetate=1:1)
  7. concentrationThe purified product was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-a8053f3dc7b74f58bf99b4d9163ce573
Source dataset
uspto-grants-2013_01
Patent number
US08362252B2

Reaction notes

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