Sodium Hydroxide → HCID 28606431, compound

HRID 1799400Notes

Reaction equation

HRID 1799400 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH:13]3[CH2:15][CH2:14]3)=[C:11]([C:16]([O:18]CC)=[O:17])[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([CH:13]3[CH2:14][CH2:15]3)=[C:11]([C:16]([OH:18])=[O:17])[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57437901HCID 57437901, compound2×

Product 1

HCID 28606431HCID 28606431, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 1-(4-bromophenyl)-5-cyclopropyl-pyrazole-4-carboxylate (Intermediate #31) (423 mg, 1.29 mmol) was dissolved in methanol (20 mL) and treated with 2M aqueous sodium hydroxide solution (3.23 mL, 6.46 mmol). The mixture was stirred at ambient temperature for 24 h and then the methanol was removed by evaporation under reduced pressure. The residue was dissolved in water (50 mL), acidified to pH4 with 2M HCl and extracted with EtOAc (3×25 mL). The combined extracts were washed with water and brine, dried (MgSO4) and evaporated to leave 1-(4-bromophenyl)-5-cyclopropyl-pyrazole-4-carboxylic acid a white solid. (343 mg, 87%).

Workup

  1. customthe methanol was removed by evaporation under reduced pressure
  2. dissolutionThe residue was dissolved in water (50 mL)
  3. extractionextracted with EtOAc (3×25 mL)
  4. washThe combined extracts were washed with water and brine
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-c800f94a85944a0097c741184ee73ad8
Source dataset
uspto-grants-2013_01
Patent number
US08344016B2

Reaction notes

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