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Paper | Regular issue | Vol 41, No. 2, 1995, pp.345-352
Published online, 1st January, 1970
DOI: 10.3987/COM-94-6959
Synthesis of 4-Hydroxy-1-methylbenzimidazole and 7-Hydroxy-1-methylbenzimidazole

Alan R. Katritzky*, Richard P. Musgrave, Bogumila Rachwal, and Chris Zaklika

*Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, U.S.A.


4-Hydroxy-1-methylbenzimidazole (1) was synthesised via condensation of 2-amino-3-nitrophenol (3) with trimethyl orthoformate, reduction of the resulting 4-nitrobenzoxazole (4) to amine (5), reaction with hydroxymethylbenzotriazole to form benzotriazolyl adduct (6), reduction to give 4-methylaminobenzoxazole (7), and finally base catalyzed rearrangement. The synthesis of 7-hydroxy-1-methylbenzimidazole (2) was accomplished by reduction of 4 with sodium borohydride to form 3-nitro-2-methylaminophenol (8), followed by hydrogenation to give amino derivative (9) and condensation with trimethyl orthoformate.