Methyl 4-imidazolecarboxylate

Chemical Properties

White crystalline powder

Uses

Methyl 4-imidazolecarboxylate was used as a starting material in the synthesis of 1-(3-prop-1-enyl)-imidazole-4-carboxyaldehyde and osmium(2,2′-bipyridyl)2(methyl 4-imidazolcarboxylate)dichloride.

General Description

Methyl 4-imidazolecarboxylate is an alkyl ester of imidazole carboxylic acid.

Synthesis

Step 1 Synthesis of methyl 1H-imidazole-4-carboxylate: 1H-imidazole-4-carboxylic acid (1.0 g, 8.9 mmol) was mixed with concentrated sulfuric acid (1 mL) in methanol (30 mL), stirred and heated to 0 °C. The reaction mixture was reacted under reflux conditions overnight. Upon completion of the reaction, the mixture was concentrated under reduced pressure and subsequently partitioned between cold water and ethyl acetate. The organic layer was separated and concentrated under reduced pressure to afford methyl 1H-imidazole-4-carboxylate (1 g, 89% yield).

References

[1] Patent: US2010/160323, 2010, A1. Location in patent: Page/Page column 23-24
[2] Patent: CN108314654, 2018, A. Location in patent: Paragraph 0086-0088
[3] Inorganic Chemistry Communications, 2017, vol. 78, p. 32 - 36
[4] Patent: WO2012/143599, 2012, A1. Location in patent: Page/Page column 79