Lithium Hydroxide → 4-chloro-5-ethyl-1H-imidazole-2-carboxylic acid

HRID 43432Notes

Reaction equation

HRID 43432 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([C:9]([O:11]CC)=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8].[OH-].[Li+]>CO.ClCCl>[Cl:1][C:2]1[N:3]=[C:4]([C:9]([OH:11])=[O:10])[NH:5][C:6]=1[CH2:7][CH3:8]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67549841ethyl 4-chloro-5-ethyl-1H-imidazole-2-carboxylate

Product 1

HCID 675489294-chloro-5-ethyl-1H-imidazole-2-carboxylic acidYield 107.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

Ethyl 4-chloro-5-ethyl-1H-imidazole-2-carboxylate obtained in Example (1c) (0.52 g, 2.56 mmol) was dissolved in methanol (8 mL) and dichloromethane (2 mL), and the solution was slowly added dropwise to a 3 N aqueous lithium hydroxide solution (3.5 mL, 10.5 mmol) heated to 70° C. Following stirring at that temperature for 40 minutes, the reaction solution was concentrated under reduced pressure and 1 N hydrochloric acid was added dropwise until the pH was 7. Thereafter, purification by reverse phase silica gel column chromatography (elution solvent: distilled water) gave 0.48 g of the title compound as a white solid (100%).

Workup

  1. concentrationthe reaction solution was concentrated under reduced pressure and 1 N hydrochloric acid
  2. additionwas added dropwise until the pH was 7
  3. customThereafter, purification
  4. washby reverse phase silica gel column chromatography (elution solvent: distilled water)

Sources & evidence

ORD record
ord-cdc364b1f03f48c18b329d8e9d48e6d0
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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