[Cl:1][C:2]1[C:7]([CH2:8][O:9][CH2:10][CH3:11])=[CH:6][C:5]([N+:12]([O-])=O)=[C:4]([F:15])[CH:3]=1.[H][H]>C(O)(=O)C.[Pt]>[Cl:1][C:2]1[C:7]([CH2:8][O:9][CH2:10][CH3:11])=[CH:6][C:5]([NH2:12])=[C:4]([F:15])[CH:3]=1A solution of 4-chloro-5-ethoxymethyl-2-fluoronitrobenzene (0.9 g, 0.0039 mole) in glacial acetic acid (50 ml) was added to a 250 ml Parr bottle containing platinum IV oxide (0.3 g) under a nitrogen atmosphere. The Parr bottle was placed on a Parr hydrogenation apparatus and charged with hydrogen. The reaction mixture was allowed to shake until hydrogen absorption ceased. The catalyst was removed by vacuum filtration. The 4-chloro-5-ethoxymethyl-2-fluoroaniline produced was used in the next step in acetic acid solution without being isolated.
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