2-[[(2-Methyl-4-nitrophenyl)sulfanyl]methyl]pyridine → 3-Methyl-4-[(2-pyridinylmethyl)sulfanyl]aniline

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Reaction Steps

To 2-[[(2-methyl-4-nitrophenyl)sulfanyl]methyl]pyridine (3.1 g) were added acetic acid (24.4 ml) and then, reduced iron (9.15 g), and the mixture was stirred for 16 hours at room temperature. The mixture was filtered with Celite, and washed with ethyl acetate. The solvent was removed under reduced pressure, and water was added to the obtained residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by silica gel column chromatography, to give 3-methyl-4-[(2-pyridinylmethyl)sulfanyl]aniline (1.4 g).

Provenance & Evidence