[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][C:9]([C:11](OC)=[O:12])=[CH:10][C:5]=2[N:4]=[CH:3]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>C1COCC1>[OH:12][CH2:11][C:9]1[CH:8]=[CH:7][C:6]2[N:2]([CH3:1])[CH:3]=[N:4][C:5]=2[CH:10]=1A solution of methyl 1-methylbenzimidazole-5-carboxylate (1.6 g, 8.42 mmol) in dry THF (80 mL) was treated with LiAlH4 (1.59 g, 42.1 mmol) and the mixture stirred for 2 hours. 1.5 mL of 5% NaOH solution was then added, and the solid which precipitated was filtered through diatomaceous earth. The filtrate was collected and the solvent removed under reduced pressure to give 0.8 g of the title compound.
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