Ethanol → 1-(4-Methylphenyl)-3-oxo-2,3-dihydro-1H-pyrazole-4-carboxylic acid

HRID 485689Notes

Reaction equation

HRID 485689 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]([CH3:18])=[CH:14][CH:13]=2)[CH:7]=1)=[O:5])C.C(O)C>[OH-].[Na+]>[CH3:18][C:15]1[CH:14]=[CH:13][C:12]([N:8]2[CH:7]=[C:6]([C:4]([OH:5])=[O:3])[C:10](=[O:11])[NH:9]2)=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 20269045HCID 20269045, compound

Product 1

HCID 202690301-(4-Methylphenyl)-3-oxo-2,3-dihydro-1H-pyrazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

The ester prepared in (b) above (245 mg, 0.99 mmol) in 2.5N sodium hydroxide (5 ml) and ethanol (1 ml) was stirred at reflux under nitrogen for 0.75 hours. and then allowed to cool. The solution was washed with ethylacetate and then acidified to pH 1.5 (5 N HCl), whereupon the title compound precipitated out, was filtered and was washed with water. Drying in vacuum gave (183 mg). νmax (Nujol) 1655, 1580, 1525, 1325, 1140, 100, cm-1. δ(CD3OD+Drop D6DMSO) 2.38 (3H,s, p-CH3), 7.50 (4H, ABq, J9 Hz, aryl protons) 8.55 (1H,s,C3 pyrazole proton). Found:M+, 2.8.0696; C11H10N2O3 requires M,218.0691.

Workup

  1. temperatureat reflux under nitrogen for 0.75 hours
  2. temperatureto cool
  3. washThe solution was washed with ethylacetate
  4. customprecipitated out
  5. filtrationwas filtered
  6. washwas washed with water
  7. customDrying in vacuum
  8. customgave (183 mg)

Sources & evidence

ORD record
ord-fa4eb7b58ce249dfa89e6fd44a41f39f
Source dataset
uspto-grants-1985_08
Patent number
US04537886

Reaction notes

Loading…