Ethanol → HCID 58508576, compound

Participants

Reaction Steps

Water (0.56 mL), ammonium chloride (18 mg), and iron powder (94 mg) were added to an ethanol (2.1 mL) suspension of methyl 4-(furan-2-yl)-2-nitrobenzoate (0.14 g), followed by heating to reflux for 2 hours and 30 minutes. The reaction mixture was cooled to room temperature, and then ammonium chloride (18 mg), iron powder (31 mg), and water (0.28 mL) were added thereto, followed by heating to reflux for 1 hour. The reaction mixture was cooled to room temperature, and then the solvent was evaporated under reduced pressure. A saturated aqueous solution of sodium bicarbonate and ethyl acetate were added to the obtained residue, and the insoluble substance was removed by filtration. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 99-95% hexane/ethyl acetate] to obtain 78 mg of methyl 2-amino-4-(furan-2-yl)benzoate as a light yellow solid.

Provenance & Evidence