N[C:2]1[CH:3]=[C:4]([NH:17][C:18](=[O:20])[CH3:19])[CH:5]=[CH:6][C:7]=1[C:8]([CH3:16])([CH3:15])[CH2:9][O:10][CH2:11][CH2:12][O:13][CH3:14].N([O-])=[O:22].[Na+]>OS(O)(=O)=O>[OH:22][C:2]1[CH:3]=[C:4]([NH:17][C:18](=[O:20])[CH3:19])[CH:5]=[CH:6][C:7]=1[C:8]([CH3:16])([CH3:15])[CH2:9][O:10][CH2:11][CH2:12][O:13][CH3:14]To a solution of N-{3-amino-4-[2-(2-methoxy-ethoxy)-1,1-dimethyl-ethyl]-phenyl}-acetamide (1.6 g, 5.7 mmol) in H2SO4 (15%, 6 mL) was added NaNO2 at 0-5° C. The mixture was stirred at this temperature for 20 min and then poured into ice water. The mixture was extracted with EtOAc (30 mL×3). The combined organic layers were washed with water and brine, dried over Na2SO4 and concentrated. The residue was purified by column chromatography (petroleum ether—EtOAc, 100:1) to give N-{3-hydroxy-4-[2-(2-methoxy-ethoxy)-1,1-dimethyl-ethyl]-phenyl}-acetamide (0.7 g, 38%).
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