Potassium Carbonate → 1-Methyl-4-phenyl-1H-imidazole-5-carboxylic acid

HRID 32509Notes

Reaction equation

HRID 32509 reaction equation
[C:1](=[O:4])([O-])[O-:2].[K+].[K+].[CH3:7][N:8]1[C:12](C=O)=[C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:10]=[CH:9]1.[Mn]([O-])(=O)(=O)=O.[K+]>CC(C)=O.O>[CH3:7][N:8]1[C:12]([C:1]([OH:2])=[O:4])=[C:11]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:10]=[CH:9]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 516875Potassium PermanganateHCID 103975361-Methyl-4-phenyl-1H-imidazole-5-carbaldehyde2×

Product 1

HCID 179657941-Methyl-4-phenyl-1H-imidazole-5-carboxylic acidYield 69%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

Potassium carbonate (3.13 g) was added to 1-methyl-4-phenyl-1H-imidazole-5-carbaldehyde (intermediate 2) (2.33 g) dissolved in acetone (125 mL) and water (25 mL). Once dissolved, potassium permanganate (4.23 g) was added and the mixture stirred for 24 hours. The mixture was filtered through diatomaceous earth and the cake washed with water (2×20 mL). Acetone was evaporated from the filtrate which was extracted with EtOAc (50 mL). The aqueous layer was acidified with acetic acid to pH 5, reduced to half volume and a cream precipitate filtered and dried at 60° C. in vacuo to give the title compound as a cream solid (1.74 g, 69%);

Workup

  1. dissolutionOnce dissolved
  2. filtrationThe mixture was filtered through diatomaceous earth
  3. washthe cake washed with water (2×20 mL)
  4. customAcetone was evaporated from the filtrate which
  5. extractionwas extracted with EtOAc (50 mL)
  6. filtrationa cream precipitate filtered
  7. customdried at 60° C. in vacuo

Sources & evidence

ORD record
ord-4fc83ac4db7047f29c95748c7bbc6c51
Source dataset
uspto-grants-2008_09
Patent number
US07427616B2

Reaction notes

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