[Cl:1][C:2]1[CH:25]=[CH:24][C:5]2[CH2:6][CH2:7][CH:8]3[C:13]([C:4]=2[CH:3]=1)=[N:12][N:11]([C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=1)[C:10](=[O:23])[CH2:9]3.Cl>C(O)C.O.[Fe]>[NH2:20][C:17]1[CH:18]=[CH:19][C:14]([N:11]2[C:10](=[O:23])[CH2:9][CH:8]3[C:13]([C:4]4[CH:3]=[C:2]([Cl:1])[CH:25]=[CH:24][C:5]=4[CH2:6][CH2:7]3)=[N:12]2)=[CH:15][CH:16]=1To a mixture of 9-chloro-2-(4-nitrophenyl)-4,4a,5,6-tetrahydrobenzo[h]cinnolin-3(2H)-one in ethanol and water is added iron powder with stirring at room temperature. To the mixture is added dropwise concentrated hydrochloric acid with stirring and heating up to 60° C. on a water bath. The resulting mixture is further stirred under heating at the same temperature and filtered, then the filtrate is concentrated. After the residue is made alkaline by adding an aqueous solution of sodium hydroxide, the mixture is extracted with chloroform. The extract is washed with water and dried over magnesium sulfate anhydride. The chloroform is distilled off to give 2-(4-aminophenyl)-9-chloro-4,4a,5,6-tetrahydrobenzo[h]cinnolin-3(2H)-one.
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