Hydrochloric Acid → 1-Benzyl-5-methyl-1H-imidazole-4-carboxylic acid

HRID 1428985Notes

Reaction equation

[CH2:1]([N:8]1[C:12]([CH3:13])=[C:11]([C:14]([O:16]CC)=[O:15])[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].Cl>CO>[CH2:1]([N:8]1[C:12]([CH3:13])=[C:11]([C:14]([OH:16])=[O:15])[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Part A: To a magnetically stirred solution of ethyl N-benzyl-5-methyl-1H-imidazole-4-carboxylate (8.4 gram, 0.0345 mol) in methanol (200 ml) was slowly added a solution of KOH (7.3 gram, 85% grade, 0.110 mol) and the resulting mixture was heated at 80° C. for 2 hours. The solution was cooled to room temperature and concentrated HCl (9.2 ml) was subsequently added. The formed precipitate was collected by filtration to give N-benzyl-5-methyl-1H-imidazole-4-carboxylic acid (6.77 gram, 91% yield). Melting point: 292° C. (decomposition).

Workup

temperatureThe solution was cooled to room temperature
filtrationThe formed precipitate was collected by filtration

Sources & evidence

ORD record: ord-e8ceffc561df494b95e80787f3aff0af
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08937184B2

Reaction notes

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