Definition
ChEBI: 5-hydroxybenzimidazole is a member of the class of benzimidazoles that is 1H-benzimidazole carrying a single hydroxy substituent at position 5. It has a role as a human metabolite, a rat metabolite and a bacterial metabolite. It is a member of benzimidazoles and a member of phenols. It derives from a hydride of a 1H-benzimidazole.
Synthesis
General procedure for the synthesis of 1H-benzimidazol-5-ol from 5-methoxybenzimidazole: 5-methoxybenzimidazole (500 mg, 3.374 mmol) was dissolved in 48% hydrobromic acid (10 mL) and the reaction was carried out at reflux for 2 hours. After completion of the reaction, the mixture was cooled to room temperature and the solvent was removed by rotary evaporator under reduced pressure. The residue was azeotropically treated with toluene (50 mL) to give the final title compound 1H-benzimidazol-5-ol as a brown solid (701 mg, 96% yield).
References
[1] Patent: WO2007/76034, 2007, A2. Location in patent: Page/Page column 125
[2] Journal of the American Chemical Society, 1955, vol. 77, p. 5192
[3] Synthetic Communications, 2010, vol. 40, # 12, p. 1765 - 1771
[4] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 7, p. 2620 - 2623
