反应详情

温度

120 °C

Sodium hydride (0.92 g, 0.023 mol; 60% suspension in mineral oil) was added portionwise to a stirred solution of 3-(4-nitrophenyl)-3-oxopropionic acid ethyl ester (5.46 g, 0.023 mol) in dimethylacetamide (20 mL) at room temperature. A solution of isatoic anhydride (3.4 g, 0.02 mol) in dimethylacetamide (20 mL) was added to this solution. The reddish mixture was stirred at 120° C. for 30 min and then the solvent was concentrated in vacuo. The crude solid was partitioned between water and ethyl acetate and the organic phase then separated. The combined organic extracts were dried over sodium sulfate and concentrated in vacuo to leave a residue which was washed once with cold tert-butylmethyl ether to yield 2-(4-nitrophenyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester (1.61 g, 28%) as a white solid, LCMS m/z 339.33 [M+H]+ @ RT 1.16 min, 100% purity.

1. concentrationthe solvent was concentrated in vacuo
2. customThe crude solid was partitioned between water and ethyl acetate
3. customthe organic phase then separated
4. dry with materialThe combined organic extracts were dried over sodium sulfate
5. concentrationconcentrated in vacuo
6. customto leave a residue which
7. washwas washed once with cold tert-butylmethyl ether