[CH3:1][NH:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[C:6]([O:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=2[F:21])[CH:5]=1.[Cl-].[NH4+]>C(O)C.O.[Fe]>[CH3:1][NH:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([O:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=2[F:21])[CH:5]=1A mixture of N-methyl-3-(2,4-difluorophenoxy)-4-nitrobenzamide (0.85 g), iron powder (0.8 g) and ammonium chloride (80 mg) in ethanol (20 ml) and water (10 ml) was refluxed with stirring for an hour. The insoluble materials were filtered, and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate, washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, and concentrated to give a powder of N-methyl-4-amino-3-(2,4-difluorophenoxy)benzamide (0.77 g).
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