Benzyl Bromide → 3,4-Dibenzyloxy aniline

Participants

Reaction Steps

3,4-Dihydroxy-1-nitrobenzene was benzylated by refluxing with benzyl bromide with potassium carbonate as a base in acetone which on reduction with sodium dithionite gave 3,4-dibenzyloxy aniline. This was coupled to 2-oxo-2,3-dihydro-1H-benzoimidazole-5-carboxylic acid using N,N-1,3-diisopropylcarbodiimide in the presence of 1-hydroxybenzotriazole to provide the amide. The amide was then debenzylated by hydrogenation in presence of palladium on carbon.

Provenance & Evidence