[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.Cl.[Sn].[OH-].[Na+]>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]=[CH:9][C:10]2[CH:11]=[CH:12][C:13]([NH2:16])=[CH:14][CH:15]=2)=[CH:6][CH:7]=1A solution of 7.3 g (30 mmol) of 4-[2-(4-fluoro-phenyl)-vinyl]-1-nitro-benzene in 250 ml of ethanol is treated with 80 ml of aqueous 25% hydrochloric acid. The mixture is heated at 110° C. and 5 g (42 mmol) of tin is added portionwise. After stirring for 3 h at 110° C. the suspension is cooled to room temperature, neutralised by additon of aqueous sodium hydroxide and extracted 3 times with dichloromethane. Drying over magnesium sulfate and evaporations yields 5.46 g (85%) of a colorless solid. MS: m/e=214.2 (M++H).
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