Hydrochloric Acid → 5-bromo-1-phenyl-1H-pyrazole-4-carboxylic acid

HRID 1731255Notes

Reaction equation

HRID 1731255 reaction equation
[Br:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1[C:13]([O:15]CC)=[O:14].[OH-].[K+].Cl>C(O)C>[Br:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1[C:13]([OH:15])=[O:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 13802165Ethyl 5-bromo-1-phenyl-1H-pyrazole-4-carboxylate

Product 1

HCID 138219315-bromo-1-phenyl-1H-pyrazole-4-carboxylic acidYield 64.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 15.5 g of 5-bromo-1-phenyl-1H-pyrazole-4-carboxylic acid, ethyl ester and 14 g of potassium hydroxide in 300 ml of 3A ethanol was refluxed for 3 hours. The solution was poured into ice water and acidified with concentrated hydrochloric acid. The precipitated solid was collected by filtration and recrystallized from ethanol/water to afford 9.0 g of 5-bromo-1-phenyl-1H-pyrazole-4-carboxylic acid. Yield 64%. mp=218°-222° C.

Workup

  1. temperaturewas refluxed for 3 hours
  2. filtrationThe precipitated solid was collected by filtration
  3. customrecrystallized from ethanol/water

Sources & evidence

ORD record
ord-083461fef2d6464ea91059f8e43a1bf7
Source dataset
uspto-grants-1986_11
Patent number
US04620865

Reaction notes

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