2-(4-Nitrobenzyl)-5-propyl-1,3,4-oxadiazole → 4-[(5-Propyl-1,3,4-oxadiazol-2-yl)methyl]aniline

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Reaction Steps

2-(4-Nitrobenzyl)-5-propyl-1,3,4-oxadiazole (7.70 g), 5% palladium carbon (7.0 g) and tetrahydrofuran (200 mL) were subjected to catalytic reduction under a hydrogen atmosphere at atmospheric pressure. The catalyst was removed by filtration, and the filtrate was concentrated. The residue was subjected to silica gel column chromatography to give 4-[(5-propyl-1,3,4-oxadiazol-2-yl)methyl]aniline as pale-yellow crystals (3.74 g, yield 55%) from a fraction eluted with hexane-ethyl acetate (1:1-1:2, v/v). Recrystallization thereof from ethyl acetate-hexane gave pale-yellow prism crystals. melting point: 60-61° C.

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