[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:6][C:7]1[C:16]2[C:11](=[C:12]([N+:20]([O-:22])=[O:21])[CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=2)[C:10]([N+:23]([O-:25])=[O:24])=[CH:9][CH:8]=1>>[ClH:6].[N+:23]([C:10]1[C:11]2[C:16](=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:12]=2[N+:20]([O-:22])=[O:21])[C:7]([N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:8][CH:9]=1)([O-:25])=[O:24]Pyrrolidine (2.5 mL) was added to 1-chloro-4,5,7-trinitronaphthalene (100 mg, 0.33 mmol, Bassilios et al, Recueil., 1962, 81, 209-214) which resulted in an immediate, highly exothermic reaction. Volatiles were removed in vacuo and purification as in 159JP06 afforded 23 mg (22%) of 159JP09 as a red solid. The product was converted to the corresponding hydrochloride salt as described above.
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