[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[C:5]([CH3:11])=[CH:4][C:3]=1[O:12][CH2:13][CH:14]1[C:16]([CH3:18])([CH3:17])[C:15]1([CH3:20])[CH3:19].C(O)(=O)C>[Fe].O>[CH3:11][C:5]1[CH:4]=[C:3]([O:12][CH2:13][CH:14]2[C:15]([CH3:19])([CH3:20])[C:16]2([CH3:18])[CH3:17])[C:2]([CH3:1])=[CH:7][C:6]=1[NH2:8]A mixture of 0.34 g of 2,5-dimethyl-4-nitro-1-[(2,2,3,3-tetramethylcyclopropyl)methoxy]benzene, 0.34 g of iron powder, 5 mL of acetic acid and 5 mL of water was stirred at 80° C. for 1 hour. The reaction mixture was cooled to around room temperature, and then concentrated under reduced pressure. The resulting residue was converted into basic with an aqueous 1 N sodium hydroxide solution, then ethyl acetate was added, and the mixture was filtered. The filtrate was extracted with ethyl acetate, and then the organic layer was washed with water and saturated salt water, and dried over anhydrous magnesium sulfate. The resulting residue was subjected to silica gel column chromatography to obtain 0.24 g of 2,5-dimethyl-4-[(2,2,3,3-tetramethylcyclopropyl)methoxy]phenylamine.
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