Ethyl 5-methoxy-1-phenyl-1H-pyrazole-4-carboxylate → 5-Methoxy-1-phenyl-1H-pyrazole-4-carboxylic acid

HRID 485679Notes

Reaction equation

HRID 485679 reaction equation
C([O:3][C:4]([C:6]1[CH:10]=[N:9][N:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:7]=1[O:17][CH3:18])=[O:5])C>[OH-].[Na+]>[CH3:18][O:17][C:7]1[N:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:9]=[CH:10][C:6]=1[C:4]([OH:5])=[O:3]

Participants

3

Reactant 1

HCID 15192739Ethyl 5-methoxy-1-phenyl-1H-pyrazole-4-carboxylate

Product 1

HCID 202690405-Methoxy-1-phenyl-1H-pyrazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

The ester prepared as described in (a) above (390 mg, 1.58 mmol) in lN sodium hydroxide (10 ml) was refluxed for 3 hours under nitrogen and then allowed to cool and the solution was washed with ethyl acetate. The aqueous layer was then acidified to pH 2(HCl) whereupon the title compound precipitated out and was filtered and washed with water followed by drying under vacuum (268 mg, 78%), νmax (Nujol) 1680, 1595, 1560 cm-1 δ (D6 -Acetone) 4.24 (3H,s,--OCH3),7.74 (5H,m, phenyl protons), 8.06 (1H,s,C5 pyrazole proton), Found M+ ; 218.0684, C11H10N2O3Requires M,218.0689.

Workup

  1. temperaturewas refluxed for 3 hours under nitrogen
  2. temperatureto cool
  3. washthe solution was washed with ethyl acetate
  4. customprecipitated out
  5. filtrationwas filtered
  6. washwashed with water
  7. dry with materialby drying under vacuum (268 mg, 78%), νmax (Nujol) 1680, 1595, 1560 cm-1 δ (D6 -Acetone) 4.24 (3H,s,--OCH3),7.74 (5H,m, phenyl protons), 8.06 (1H,s,C5 pyrazole proton), Found M+

Sources & evidence

ORD record
ord-9c9d7428cf314749885d117926dc41c5
Source dataset
uspto-grants-1985_08
Patent number
US04537886

Reaction notes

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