Uses
5-Methyl-1H-imidazole-2-carboxylic acid (cas# 70631-93-5) is a useful research chemical. It is in the chemical composition of steam and solvent crude oil extracts from azadirachta indica leaves. It is also in the slurry composition for chemical mechanical polishing of metal cable.
Definition
ChEBI: 5-methyl-imidazole-2-carboxylic acid is an imidazolyl carboxylic acid that is 1H-imidazole with methyl and carboxylic acid group substituents at positions 5 and 2 respectively. It has a role as a metabolite.
Synthesis
General procedure for the synthesis of 4-methyl-1H-imidazole-2-carboxylic acid from ethyl 4-methyl-1H-imidazole-2-carboxylate: ethyl 4-methyl-1H-imidazole-2-carboxylate (77.0 g, 0.5 mol) was dissolved in anhydrous ethanol (600 mL) at room temperature, and 250 mL of 40% aqueous sodium hydroxide was subsequently added. The reaction mixture was heated to 50 °C and maintained at this temperature for the reaction. Upon completion of the reaction, it was cooled to room temperature, neutralized and acidified with 37% concentrated hydrochloric acid to pH=6. The solvent was removed by distillation under reduced pressure and the resulting residue was purified by column chromatography using dichloromethane/methanol (10:1, v/v) as eluent to give the final 4-methyl-1H-imidazole-2-carboxylic acid (60.2 g, 96% yield) as a white solid.
References
[1] Patent: CN104016925, 2016, B. Location in patent: Paragraph 0028-0030; 0038; 0039
[2] Journal of Heterocyclic Chemistry, 2018, vol. 55, # 11, p. 2619 - 2622
