[CH2:1]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:16][C:17]3[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=3[N:19]=2)=[CH:11][C:10]=1[N+:24]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C.C(O)C.C(=O)([O-])O.[Na+]>[Fe].C(Cl)(Cl)Cl>[CH2:1]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:16][C:17]3[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=3[N:19]=2)=[CH:11][C:10]=1[NH2:24])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
To a suspension of 2-(4-benzylamino-3-nitrophenyl)benzoxazole (see Working Example 17-1) (340 mg, 0.985 mmol) was added 10% aqueous acetic acid solution (5 mL), ethanol (8 mL), and iron powder (165 mg, 2.95 mmol), and this was heated to reflux with stirring for 4 hours. After the reaction was complete, saturated aqueous sodium hydrogen carbonate solution and chloroform were added, this was filtered through Celite and then extracted with chloroform. The organic layer obtained was dried over anhydrous sodium sulfate, filtered, and concentrated to give an oil that was purified by silica gel column chromatography to yield the title compound (87 mg, 28% yield) as brown crystals.
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