Sulfuric Acid → HCID 178424504, 화합물

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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 (1×20 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).

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