反应详情

温度

120 °C

6-Methoxy-3-nitroquinoline (Magnus, P. et al., J. Am. Chem. Soc. 119, 5591, 1997; 100 mg, 0.49 mmol) was dissolved in hydrogen bromide solution (47% aq, 2.5 mL, 0.2 M), heated and stirred at 120° C. for 16 hours. The reaction mixture was cooled to room temperature, neutralized with 6N NaOH, then extracted with EtOAc (150 mL). The organic layer was dried over Na2SO4 and purified by flash chromatography (SiO2, 40-50% EtOAc/hexanes), obtaining 73 mg (78%) of 6-hydroxy-3-nitroquinoline. LC/MS (m/z): 190.9 (MH+), Rt 1.97 minutes.

1. temperatureheated
2. temperatureThe reaction mixture was cooled to room temperature
3. extractionextracted with EtOAc (150 mL)
4. dry with materialThe organic layer was dried over Na2SO4
5. custompurified by flash chromatography (SiO2, 40-50% EtOAc/hexanes)