[CH3:1][N:2]([CH3:17])[C:3]1[CH:8]=[C:7]([Cl:9])[C:6]([CH:10]=[C:11]([N+:13]([O-])=O)[CH3:12])=[C:5]([Cl:16])[CH:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1.CCOCC>[ClH:9].[ClH:9].[Cl:9][C:7]1[CH:8]=[C:3]([N:2]([CH3:1])[CH3:17])[CH:4]=[C:5]([Cl:16])[C:6]=1[CH2:10][CH:11]([NH2:13])[CH3:12]
A solution of 13.7 g of N,N-dimethyl-3,5-dichloro-4-(2-nitropropenyl)aniline in 150 ml of dry tetrahydrofuran is added dropwise with stirring to 8.0 g lithium aluminum hydride in 200 ml of dry ether. The mixture is then refluxed for 4 hours. 40 ml of saturated sodium sulphate solution is added dropwise and the mixture is filtered. The filtrate is dried over anhydrous sodium sulphate and acidified with hydrogen chloride. The precipitated salt is filtered off and washed with ether. Yield: 15.2 g, m.p. 195°-197°. The product is recrystallized from aqueous ethanol-isopropyl ether. Yield: 11.9 g, m.p. 199°-200°.
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