反应详情

温度

50 °C

To a solution of 3-Hydroxy-6-methylquinoline (92) (348 mg, 2.19 mmol) in DMF (3.5 mL), was added NaH (60% oil suspension, 90 mg, 2.25 mmol) in one portion at room temperature. After 5 min 3,4,5-trichloronitrobenzene (509 mg, 2.25 mmol) in DMF (2 mL) was added and the reaction mixture was heated at 50° C. with stirring for 2 h. After cooling to room temperature. Ice/water was added to the reaction mixture, which was then acidified with 2N HCl and extracted twice with AcOEt. Organic layer was washed with brine, dried over anhydrous MgSO4, and concentrated. Crude residue was purified by column chromatography (hexane/AcOEt4/1, 80 g of silica gel) to afford compound 93 (510 mg, 67%). 1H NMR (300 MHz, DMSO-d6) δ 7.52-7.57 (2H, m), 7.61 (1H, s), 7.94 (1H, d, J=8.6 Hz), 8.63 (2H, s), 8.86 (1H, d, J=2.9 Hz).

1. temperatureAfter cooling to room temperature
2. extractionextracted twice with AcOEt
3. washOrganic layer was washed with brine
4. dry with materialdried over anhydrous MgSO4
5. concentrationconcentrated
6. customCrude residue was purified by column chromatography (hexane/AcOEt4/1, 80 g of silica gel)