Methyl 2-(4-cyano-2-nitrophenyl)acetate → 2-Oxindole-6-carbonitrile

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Methyl (4-cyano-2-nitrophenyl)acetate (128 mg) was dissolved in AcOH (3.0 ml), followed by addition of iron powders (129 mg), and the reaction solution was stirred in an oil bath at 100° C. for 1.5 hours. It was concentrated to remove AcOH, followed by addition of EtOAc. The brown solid was separated by filtration, and the organic layer was washed with a 1M HCl solution and saturated brine, dried over anhydrous MgSO4, and concentrated. The residue was purified by silica gel column chromatography (chloroform:CH3OH=99:1 to 95:5) to obtain to obtain 2-oxoindoline-6-carbonitrile (52.0 mg) as a pale yellow solid.

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