Sodium Sulfate → HCID 86588583, compound

HRID 2084067Notes

Reaction equation

HRID 2084067 reaction equation
O=[C:2]([C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)[CH2:3][N:4]1[CH2:8][CH2:7][CH2:6][C:5]1=[O:9].Cl.[NH2:17][OH:18].S([O-])([O-])(=O)=O.[Na+].[Na+]>CO.O>[OH:18][N:17]=[C:2]([C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)[CH2:3][N:4]1[CH2:8][CH2:7][CH2:6][C:5]1=[O:9]

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 443297Hydroxyamine hydrochlorideHCID 22733081HCID 22733081, compound

Product 1

HCID 86588583HCID 86588583, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

To 0.3 g (1.47 mmol) of 1-(2-oxo-2-pyridin-3-yl-ethyl)-pyrrolidin-2-one prepared from Example 20, 0.15 g (2.21 mmol) of hydroxylamine hydrochloride salt and 0.12 g of sodium sulfate were added in methanol/water (1.5:1). The mixture was reacted at 30˜40° C. for 12˜36 hours. Upon completion of the reaction, the reaction mixture was concentrated under reduced pressure, extracted with ethyl acetate for three times, washed with brine for two times, and dried over sodium sulfate. After concentrating under reduced pressure, it was purified by separation with silica gel column chromatography (chloroform/methanol (30:1˜10:1)) to obtain 0.21 g (66% yield) of 1-(2-hydroxyimino-2-pyridin-3-yl-ethyl)-pyrrolidin-2-one as E/Z mixture (1.56:1).

Workup

  1. customThe mixture was reacted at 30˜40° C. for 12˜36 hours
  2. customUpon completion of the reaction
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. extractionextracted with ethyl acetate for three times
  5. washwashed with brine for two times
  6. dry with materialdried over sodium sulfate
  7. concentrationAfter concentrating under reduced pressure, it
  8. customwas purified by separation with silica gel column chromatography (chloroform/methanol (30:1˜10:1))

Sources & evidence

ORD record
ord-d9aee380199643a790ed9af95b2ba73c
Source dataset
uspto-grants-2004_04
Patent number
US06716857B2

Reaction notes

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