Hydrochloric Acid → 4-bromo-1H-imidazole-5-carboxylic acid

HRID 1874851Notes

Reaction equation

HRID 1874851 reaction equation
[Br:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[C:7]([O:9]C)=[O:8].[OH-].[Na+].Cl>CO>[Br:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[C:7]([OH:9])=[O:8]

Participants

5

Procedure

A solution of methyl 4-bromo-1H-imidazole-5-carboxylate (0.708 g, 3.5 mmol) was stirred in a solution of MeOH (20 mL) and 2N NaOH (20 mL, 40 mmol) at 40° C. for 4 h, then additional 2N NaOH (20 mL, 40 mmol) was added and the reaction mixture kept at 40° C. for another hour. The reaction mixture was then acidified by addition of 1M HCl (100 mL) and extracted with EtOAc. The organic extracts were dried (Na2SO4), and the solvent was evaporated to provide crude 4-bromo-1H-imidazole-5-carboxylic acid (0.156 g, 24%) as a white solid which was used without further purification.

Workup

  1. waitthe reaction mixture kept at 40° C. for another hour
  2. extractionextracted with EtOAc
  3. dry with materialThe organic extracts were dried (Na2SO4)
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-e5ee5e0b61a749c09a757c2c850a2040
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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