HCID 16638017, compound → 1-(4-Nitrophenyl)-3-oxo-2,3-dihydro-1H-pyrazole-4-carboxylic acid

HRID 485683Notes

Reaction equation

HRID 485683 reaction equation
C([O:3][C:4]([C:6]1[C:10](=[O:11])[NH:9][N:8]([C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)[CH:7]=1)=[O:5])C>[OH-].[Na+]>[N+:18]([C:15]1[CH:16]=[CH:17][C:12]([N:8]2[CH:7]=[C:6]([C:4]([OH:5])=[O:3])[C:10](=[O:11])[NH:9]2)=[CH:13][CH:14]=1)([O-:20])=[O:19]

Participants

3

Reactant 1

HCID 16638017HCID 16638017, compound

Product 1

HCID 202690391-(4-Nitrophenyl)-3-oxo-2,3-dihydro-1H-pyrazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

The ester prepared as in (a) above (300 mg, 1.08 mmol) in 0.5N sodium hydroxide (20 ml) was stirred under nitrogen at reflux for 1 hour. The reaction mixture was allowed to cool, washed with ethyl acetate and then acidified to pH 1.5. The aqueous solution was then extracted with ethyl acetate which on drying (MgSO4) and evaporation followed by ether trituration produced the title compound (267 mg). νmax (Nujol) 1680, 1615, 1499, 1580 cm-1, δ(CD3OD+D6DMSO) 8.30 (4H, ABq, J10 Hz, aryl protons), 8.86(1H, s, C3 pyrazole proton). Found: M+, 249.0386; C10H7N3O5 requires M, 249.0386.

Workup

  1. temperatureat reflux for 1 hour
  2. temperatureto cool
  3. washwashed with ethyl acetate
  4. extractionThe aqueous solution was then extracted with ethyl acetate which
  5. customon drying
  6. custom(MgSO4) and evaporation

Sources & evidence

ORD record
ord-846f530e6e504042893f1abee6b39797
Source dataset
uspto-grants-1985_08
Patent number
US04537886

Reaction notes

Loading…