Methanol → 1-(4-Methoxyphenyl)-3-methyl-1H-pyrazole-5-carboxylic acid

HRID 1013055Notes

Reaction equation

HRID 1013055 reaction equation
C([O:3][C:4]([C:6]1[N:7]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[N:8]=[C:9]([CH3:11])[CH:10]=1)=[O:5])C.CO.C1COCC1.[OH-].[Na+]>O>[CH3:19][O:18][C:15]1[CH:14]=[CH:13][C:12]([N:7]2[C:6]([C:4]([OH:5])=[O:3])=[CH:10][C:9]([CH3:11])=[N:8]2)=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 11021617Ethyl 1-(4-methoxyphenyl)-3-methyl-1H-pyrazole-5-carboxylate

Product 1

HCID 27695991-(4-Methoxyphenyl)-3-methyl-1H-pyrazole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2-(4-Methoxy-phenyl)-5-methyl-2H-pyrazole-3-carboxylic acid ethyl ester (400 mg) in a 1:1:1 mixture of MeOH:THF:water was added 10% NaOH (20 mL). The mixture was heated to reflux and the reaction monitored by TLC and HPLC until hydrolysis was complete. The solution was cooled and concentrated under reduced pressure. The residue was acidified with 10% HCl and extracted with EtOAc. The organic fractions were combined and dried over MgSO4 and concentrated under reduced pressure. The resulting solid was used without further purification (Yield 242 mg). LC-MS (C12H12N2O3 calculated 232) m/z 231 (M−H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. customthe reaction monitored by TLC and HPLC until hydrolysis
  4. temperatureThe solution was cooled
  5. concentrationconcentrated under reduced pressure
  6. extractionextracted with EtOAc
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting solid was used without further purification (Yield 242 mg)

Sources & evidence

ORD record
ord-859d09d23e40448a8f4f7d487ff65009
Source dataset
uspto-grants-2011_07
Patent number
US07981896B2

Reaction notes

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