反应详情

3.5 g (16 mmol) of ethyl 2-oxo-1,2-dihydroquinoline-3-carboxylate was dissolved in a mixed solvent of N,N-dimethylformamide (80 mL) and 1,2-dimethoxyethane (25 mL), and under a nitrogen gas stream, 0.71 g (18 mmol) of 60% sodium hydride (oily) was added to the solution at room temperature. The mixture was stirred for 15 minutes at room temperature. 5.6 g (64 mmol) of lithium bromide was added to the above mixture at room temperature, and the resulting mixture was stirred for 15 minutes at room temperature. 4.6 g (32 mmol) of iodomethane was further added to the mixture at room temperature, and the resulting mixture was stirred for 3 hours at 60° C. The reaction mixture was poured into an aqueous solution of citric acid, and the mixture was extracted with ethyl acetate. The organic phase was washed with brine, an aqueous solution of sodium hydrogen carbonate, and brine in this order, and was dried and concentrated. The residue was purified by column chromatography (ethyl acetate:n-hexane=1:4 to 4:1), and thus 2.4 g (yield: 64%) of the title compound was obtained as light yellow crystals.

1. stirringthe resulting mixture was stirred for 15 minutes at room temperature
2. stirringthe resulting mixture was stirred for 3 hours at 60° C
3. extractionthe mixture was extracted with ethyl acetate
4. washThe organic phase was washed with brine
5. dry with materialan aqueous solution of sodium hydrogen carbonate, and brine in this order, and was dried
6. concentrationconcentrated
7. customThe residue was purified by column chromatography (ethyl acetate:n-hexane=1:4 to 4:1)