Hydrochloric Acid → HCID 86723048, compound

HRID 522336Notes

Reaction equation

HRID 522336 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH:13]3[CH2:16][CH2:15][CH2:14]3)=[C:11]([C:17]([O:19]C)=[O:18])[CH:10]=[N:9]2)=[CH:4][CH:3]=1.O.[OH-].[Li+].Cl>CO.C1COCC1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([CH:13]3[CH2:14][CH2:15][CH2:16]3)=[C:11]([C:17]([OH:19])=[O:18])[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 86723049HCID 86723049, compound

Product 1

HCID 86723048HCID 86723048, compoundYield 87.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methyl 1-(4-chlorophenyl)-5-cyclobutyl-pyrazole-4-carboxylate (8.3 g, 28.5 mmol) and lithium hydroxide monohydrate (3.6 g, 85.6 mmol) in MeOH (25 mL), THF (25 mL) and H2O (12 mL) was stirred at 80° C. for 1 h. After cooling to room temperature the mixture was acidified with 1 M aqueous HCl and extracted with EtOAc (400 mL). The organic layer was separated, dried over anhydrous sodium sulfate, and concentrated in vacuo to yield 1-(4-chlorophenyl)-5-cyclobutyl-pyrazole-4-carboxylic acid (6.92 g, 87% yield).

Workup

  1. temperatureAfter cooling to room temperature the mixture
  2. extractionextracted with EtOAc (400 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4c7f2ad80c654a09830331b7e3b92d12
Source dataset
uspto-grants-2016_05
Patent number
US09328116B2

Reaction notes

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