Potassium Carbonate → HCID 85433096, compound

HRID 2184760Notes

Reaction equation

HRID 2184760 reaction equation
O=[C:2]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH:18]=[CH:17][CH:16]=[N:15]2)=[CH:10][CH:9]=1)[CH2:3][CH2:4][C:5]([OH:7])=[O:6].C(=O)([O-])[O-].[K+].[K+].Cl.[NH2:26][OH:27]>C(O)C.O.CO>[OH:27][N:26]=[C:2]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH:18]=[CH:17][CH:16]=[N:15]2)=[CH:10][CH:9]=1)[CH2:3][CH2:4][C:5]([OH:7])=[O:6]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 12043167HCID 12043167, compound

Product 1

HCID 85433096HCID 85433096, compoundYield 78.5%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred suspension of 4oxo-4(4-pyrazol-1-yl-phenyl)butyric acid (Sircar I., et al., Journal of Medicinal Chemistry, 1985;28:1405-13) (0.0277 g, 0.000113 mol) in absolute ethanol (0.55 mL) at room temperature was added potassium carbonate (0.010 g, 0.000072 mol) followed by a solution of hydroxylamine hydrochloride (0.010 g, 0.00014 mol) in water (0.25 mL), and the resulting mixture was stirred for 1 day. The volatiles were rotary evaporated. The residue was dissolved in methanol, silica gel (0.35 g, 230-400 mesh) was added, and the mixture was rotary evaporated to dryness. The residue was purified by chromatography on silica gel (6.0 g, 230-400 mesh) eluting with dichloromethane-methanol (12:1,25×5 mL) to give 0.0230 g of 4-hydroxyimino-4(4pyrazol-1-yl-phenyl)-butyric acid as an off-white solid; mp 128-130° C.

Workup

  1. additionsilica gel (0.35 g, 230-400 mesh) was added
  2. customthe mixture was rotary evaporated to dryness
  3. customThe residue was purified by chromatography on silica gel (6.0 g, 230-400 mesh)
  4. washeluting with dichloromethane-methanol (12:1,25×5 mL)

Sources & evidence

ORD record
ord-e8f52a2ab8804fecbe1aadd97a6514fb
Source dataset
uspto-grants-2002_06
Patent number
US06399612B1

Reaction notes

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