Methanol → 2,5-Dimethylimidazole-4-carboxylic acid

HRID 1875110Notes

Reaction equation

HRID 1875110 reaction equation
[OH-].[Li+].[CH3:3][C:4]1[NH:5][C:6]([C:10]([O:12]CC)=[O:11])=[C:7]([CH3:9])[N:8]=1.CO>C1COCC1>[CH3:3][C:4]1[NH:5][C:6]([C:10]([OH:12])=[O:11])=[C:7]([CH3:9])[N:8]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 178470392HCID 178470392, compound

Product 1

HCID 136845092,5-Dimethylimidazole-4-carboxylic acidYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

Lithium hydroxide (1.6 mL, 1.6 mmol, 1 M in H2O) was added to a solution of ethyl 2,4-dimethyl-1H-imidazole-5-carboxylate (54 mg, 0.32 mmol) in THF:MeOH (4.8 mL/1.6 mL). The reaction mixture was heated at 70° C. for 4 h. The solvent was evaporated and dried in vacuo to give the title compound (mg, >99%) as a white solid which was directly used in the next step without purification.

Workup

  1. customThe solvent was evaporated
  2. customdried in vacuo

Sources & evidence

ORD record
ord-bb0bd8eb339a47b287c19ffe91911256
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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