Hydrochloric Acid → 3-(Furan-2-ylmethoxy)aniline

Participants

Reaction Steps

830 mg (3.8 mmol) of 3-(furan-2-ylmethyl oxy)nitrobenzene was dissolved in 10 mL of ethanol. 1.1 g (19.70 mmol) of iron and 1 mL of 1N hydrochloric acid (1.0 mmol) were added thereto and heated under reflux for 2 hours. After cooling the reaction solution to room temperature, 1.5 mL of 1N sodium hydroxide was added dropwise, and filtration through celite was carried out. The filtrate was condensed, and ethyl acetate and water were added to the filtrate to separate the solution into organic layer and aqueous layer. The organic layer was separated, washed with a saturated sodium chloride solution, and dried over magnesium sulfate. Thereafter, filtration was carried out, and the filtrate was condensed. The resulting crude product was separated and purified using silica gel column chromatography to give 3-(furan-2-ylmethoxy)aniline (yield: 86%).

Provenance & Evidence