[C:1]([O:5][C:6]1[CH:15]=[C:14]2[C:9]([CH:10]=[CH:11][CH:12]=[C:13]2[N+:16]([O-:18])=[O:17])=[CH:8][CH:7]=1)([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:20]O.[OH-].[K+].O>CCO.CO>[NH2:20][C:10]1[C:9]2[C:14](=[CH:15][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:7][CH:8]=2)[C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=1
To a stirred solution of 7-tert-butoxy-1-nitronaphthalene, as described above in Step D, (3.35 g, 13.7 mmol) and hydroxylamine hydrochloride (5.94 g, 85.5 mmol) in 95% EtOH (140 mL) at 60° C. was added KOH (11.9 g, 212 mmol) in MeOH (75 mL), dropwise over 30 min. The reaction mixture was stirred at 60° C. for 6 hours, then poured into H2O (200 mL) and extracted with CH2Cl2 (3×300 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by flash column chromatography on silica, eluting with a gradient of hexane—20% to 40% EtOAc to yield the titled product.
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