反应详情

3,4-Dihydro-2(1H)-quinolinone (1.0 g, 6.70 mmol) is dissolved in 20 mL of concentrated sulfuric acid at −10° C., and then 5 mL of water is added slowly to the solution. After 5 minutes, 61% nitric acid (0.5 mL, 6.70 mmol) is added drdpwise to the solution. The reaction mixture turns from yellow to dark red, and eventually solidifies. After 1 hour, water (50 mL) is added slowly at −10° C. and precipitate appears. The solution is poured into a separatory funnel, extracted with ethyl acetate (20 mL×2) and washed with saline (20 mL). The organic layers are collected and dried over MgSO4. Solvent is removed and the title compound is obtained as a pale yellow solid (1.0 g, 76%); 1H NMR (300 MHz, DMSO) δ 10.66 (s, 1H), 8.08-8.01 (m, 2H), 6.96 (d, 1H), 2.98 (t, 2H), 2.49 (dd, 2H).

1. waitAfter 1 hour
2. additionThe solution is poured into a separatory funnel
3. extractionextracted with ethyl acetate (20 mL×2)
4. washwashed with saline (20 mL)
5. customThe organic layers are collected
6. dry with materialdried over MgSO4
7. customSolvent is removed