[NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[N+:9]([C:12]1[CH:17]=[CH:16][C:15](F)=[CH:14][CH:13]=1)([O-:11])=[O:10].Cl>O>[N+:9]([C:12]1[CH:17]=[CH:16][C:15]([NH:1][C:2]2[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=2)=[CH:14][CH:13]=1)([O-:11])=[O:10]A mixture of 32.4 g (0.3 mol) of m-aminophenol and p-nitrofluorobenzene (0.15 mol) was boiled under reflux for 10 days in 400 ml of water and then poured into dilute hydrochloric acid, followed by extraction with ethyl acetate, washing 2 to 3 times with dilute hydrochloric acid and then concentrated. The deposited crystals were washed with hot benzene, cooled and then filtered. The yield was 26 g and the melting point was 158°-160° C.
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