[CH3:1][O:2][C:3](=[O:17])[CH2:4][O:5][C:6]1[C:11]([F:12])=[CH:10][C:9]([N+:13]([O-])=O)=[CH:8][C:7]=1[F:16].[H][H]>[Pd].O1CCCC1>[CH3:1][O:2][C:3](=[O:17])[CH2:4][O:5][C:6]1[C:7]([F:16])=[CH:8][C:9]([NH2:13])=[CH:10][C:11]=1[F:12]A slurry of (4-nitro-2,6-difluoro-phenoxy)-acetic acid methyl ester (737 mg, 2.98 mmol) and 10% palladium on carbon (200 mg) in tetrahydrofuran (40 mL) was stirred under 1 atmosphere of hydrogen gas for 7 h. The mixture was flushed with nitrogen, and filtered through a pad of celite to afford the title compound as a pale tan oil (646 mg) that solidified on standing.
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