[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[C:4]([N+:10]([O-])=O)[CH:3]=1.Cl.[Cl-].[NH4+]>CO.O.[Zn]>[NH2:10][C:4]1[CH:3]=[C:2]([Cl:1])[C:7]([CH3:8])=[CH:6][C:5]=1[OH:9]To a solution of 4-chloro-5-methyl-2-nitrophenol (5.0 g) in methanol (100 mL) at 0° C. was added zinc powder (8.71 g), which was activated by hydrochloric acid in advance, and a solution of ammonium chloride (7.1 g) in water (20 mL). The suspension was stirred for 4 h at room temperature. Then the insoluble material was filtered off through celite, and the celite cake was washed with ethyl acetate (100 mL). The filtrate and washings were combined and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel using hexane/ethyl acetate (3:2) to yield the title compound (1.4 g).
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