反应详情

To a solution of 4-[2-(2-methoxy-ethoxy)-1,1-dimethyl-ethyl]-phenylamine (5.8 g, 26 mmol) in H2SO4 (20 mL) was added KNO3 (2.63 g, 26 mmol) at 0° C. After addition was complete, the mixture was stirred at this temperature for 20 min and then poured into ice-water. The mixture was extracted with EtOAc (50 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 4-[2-(2-methoxy-ethoxy)-1,1-dimethyl-ethyl]-3-nitro-phenylamine (5 g, 71%).

1. additionAfter addition
2. extractionThe mixture was extracted with EtOAc (50 mL×3)
3. washThe combined organic layers were washed with water and brine
4. dry with materialdried over Na2SO4
5. concentrationconcentrated
6. customThe residue was purified by column chromatography (petroleum ether-EtOAc, 100:1)