Cl[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH2:12]([NH2:14])[CH3:13]>C(O)C>[CH2:12]([NH:14][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10])[CH3:13]A mixture of 26 g of 2,5-dichloro-nitrobenzene, 400 ml of ethanol and 25 ml of ethylamine was refluxed for 24 hours while adding 5 ml of ethylamine at 6 hour intervals and the mixture was cooled and filtered. The orange needles were washed with a small amount of an ethanol-ether mixture and dried over P2O5 under vacuum to obtain 24.4 g (89% yield) of N-ethyl-4-chloro-2-nitro-aniline melting at 90°-91° C.
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