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Hydrochloric Acid → 1-(4-Chlorophenyl)-5-(1-methylethyl)-1H-pyrazole-4-carboxylic acid

HRID 1754387
Notes
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Reaction equation

HRID 1754387 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH:13]([CH3:15])[CH3:14])=[C:11]([C:16]([O:18]C)=[O:17])[CH:10]=[N:9]2)=[CH:4][CH:3]=1.O.[OH-].[Li+].O.Cl>CO.C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([CH:13]([CH3:15])[CH3:14])=[C:11]([C:16]([OH:18])=[O:17])[CH:10]=[N:9]2)=[CH:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 86724388Methyl 1-(4-chlorophenyl)-5-isopropyl-pyrazole-4-carboxylate

Product 1

HCID 80788981-(4-Chlorophenyl)-5-(1-methylethyl)-1H-pyrazole-4-carboxylic acidYield 97%

Reagents, catalysts & solvents 2

HCID 887
Methanol
Solvent
HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methyl 1-(4-chlorophenyl)-5-isopropyl-pyrazole-4-carboxylate (26.0 g, 96.7 mmol) and lithium hydroxide monohydrate (10.0 g, 238 mml) in MeOH (60 mL), THF (60 mL), and H2O (30 mL) was heated at 80° C. for 3 h. The reaction mixture was cooled to room temperature, acidified with 1 N aqueous HCl, and extracted with EtOAc (600 ml). The organic layer was separated, dried over anhydrous sodium sulfate, and concentrated in vacuo to yield 1-(4-chlorophenyl)-5-isopropylpyrazole-4-carboxylic acid (24.0 g, 97%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with EtOAc (600 ml)
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d52058760a6c47a18ae51ef5c7ec3f0d
Source dataset
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09169248B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes