Ethanol → 3-(2-Cyanophenyl)-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one sulfate

HRID 2238572Notes

Reaction equation

HRID 2238572 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:10](=[O:27])[N:11]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:12]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[CH:14]=1)#[N:2].C(O)C.[OH:31][S:32]([OH:35])(=[O:34])=[O:33].C(OCC)(=O)C>C(OCC)(=O)C>[S:32]([OH:35])([OH:34])(=[O:33])=[O:31].[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:10](=[O:27])[N:11]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:12]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[CH:14]=1)#[N:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 9924495PerampanelHCID 86628183Ethyl acetate sulfuric acid

Product 1

HCID 177513363-(2-Cyanophenyl)-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one sulfateYield 154.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-(2-cyanophenyl)-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one (1.0 g, 0.687 mmol) and ethanol (small amount) was concentrated under reduced pressure, followed by adding ethyl acetate (small amount) to the residue before further concentration under reduced pressure. A 10% (v/v) H2SO4/ethyl acetate solution (0.439 mL, 0.824 mmol) was added to an ethyl acetate (15 mL) suspension containing the resultant residue, which was then stirred at room temperature for 4 days. The precipitated solid was collected by filtration, washed with ethyl acetate (small amount), and then dried under reduced pressure to provide 475 mg of the title compound as white crystals.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. additionby adding ethyl acetate (small amount) to the residue
  3. concentrationbefore further concentration under reduced pressure
  4. filtrationThe precipitated solid was collected by filtration
  5. washwashed with ethyl acetate (small amount)
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-d9bd0dd2e3ff45c0842b28e10a331aac
Source dataset
uspto-grants-2010_05
Patent number
US07718807B2

Reaction notes

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