反应详情

A sample of N-(2,5-dimethylphenyl)-4-methyl-3-oxopentanamide and 10.0 mL of H2SO4 was reacted at 100° C. for 1 hour. After the reaction was cooled to room temperature it was quenched into ice-H2O. The resulting mixture was extracted with CH2Cl2 (3×20 mL). The combined organic extracts were washed with saturated NaHCO3 (3×15 mL), brine (lx 20 mL), dried over MgSO4 and concentrated. The residue was recrystallized in EtOAc to give 1.30 g of the desired 4-isopropyl-5,8-dimethylquinolin-2-ol. Spectroscopic data: 1H NMR (300 MHz, CDCl3) δ ppm 1.29 (d, J=6.45 Hz, 6 H) 2.41 (s, 3 H) 2.77 (s, 3 H) 3.84 (quin, J=6.59 Hz, 1 H) 6.67 (s, 1 H) 6.93 (d, J=7.62 Hz, 1 H) 7.19 (d, J=7.62 Hz, 1 H) 8.81 (br. s., 1 H).

1. customwas quenched into ice-H2O
2. extractionThe resulting mixture was extracted with CH2Cl2 (3×20 mL)
3. washThe combined organic extracts were washed with saturated NaHCO3 (3×15 mL), brine (lx 20 mL)
4. dry with materialdried over MgSO4
5. concentrationconcentrated
6. customThe residue was recrystallized in EtOAc