S(=O)(=O)(O)O.[N+:6]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)=[C:11](N)[CH:10]=1)([O-:8])=[O:7].N([O-])=[O:26].[Na+]>O>[N+:6]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)=[C:11]([OH:26])[CH:10]=1)([O-:8])=[O:7]A mixture of 15.0 mL water and 11.0 mL concentrated sulfuric acid was added to 13.0 g of 4,4'-dinitro-2-aminobiphenyl, and the resulting mixture was stirred for 2 hours while heating, whereupon 26.5 g of crushed ice was added. On an ice bath, an aqueous solution of 3.51 g of sodium nitrite was added dropwise to the aforementioned mixture; the resulting system was mixed for 10 minutes and subsequently allowed to stand at quiescence for several minutes. The reaction mixture was then added dropwise to a boiling solution that had been prepared by adding 33.4 mL concentrated sulfuric acid to 25 mL of water. Boiling was continued for 5 minutes, after which the mixture was poured into a beaker on an ice bath. The filter cake afforded by suction filtration was purified by column chromatography to give 10.9 g of 4,4'-dinitro-2-hydroxybiphenyl as a yellowish brown powder.
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