[N+:1]([C:4]1[CH:21]=[CH:20][C:7]([C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=2)=[O:9])=[CH:6][CH:5]=1)([O-])=O.[H][H]>C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[CH:21]=[CH:20][C:7]([C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)=[O:9])=[CH:6][CH:5]=111.0 g of 4-nitrophenyl 4-nitrobenzoate (38.2 mM) were dissolved in 350 ml of ethyl acetate and 1.0 g of palladium on charcoal (10%) was added. The resulting mixture was hydrogenated at atmospheric pressure until the theoretical amount of hydrogen was consumed. The mixture was then filtered, the cake was washed with ethyl acetate and the filtrate was evaporated to dryness to give 8.71 g (38.2 mM, 99%) of 4-aminophenyl 4-aminobenzoate as slightly beige crystals.
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