Hydrochloric Acid → 2-Allyloxy-4-methoxyaniline

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2.09 g of 2-allyloxy-4-methoxynitrobenzene was dissolved in 20 ml of ethanol, 5 ml of THF, and 4 ml of water. Thereafter, 4.27 g of ammonium chloride and 2.23 g of iron were added to the reaction solution, and the obtained mixture was stirred while heating at 80° C. for 4 hours. Thereafter, 2 g of ammonium chloride, 1 g of iron, and 0.25 ml of 5 N HCl were added to the reaction solution, and the obtained mixture was further stirred while heating for approximately 2 hours. The reaction solution was stood to cool and then filtered through celite. A saturated sodium bicarbonate aqueous solution and ethyl acetate were added thereto, so as to separate an organic layer. The obtained organic layer was washed with a saturated sodium chloride solution and then dried over anhydrous magnesium sulfate. After removing the drying agent by filtration, the organic layer was concentrated under a reduced pressure, and the residue was then purified by NH silica gel column chromatography (hexane/ethyl acetate), so as to obtain 1.09 g of the subject compound.

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