603-85-0Relevant articles and documents
SYNTHESIS OF 4-HYDROXY-1-METHYLBENZIMIDAZOLE AND 7-HYDROXY-1-METHYLBENZIMIDAZOLE
Katritzky, Alan R.,Musgrave, Richard P.,Rachwal, Bogumila,Zaklika, Chris
, p. 345 - 352 (2007/10/03)
4-Hydroxy-1-methylbenzimidazole (1) was synthesized 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.