反应详情

温度

80 °C

Ethyl 4,6-dichloronicotinate (10.0 g, 45.44 mmol) in EtOH (100 mL) was stirred till a clear solution was obtained followed by addition of aniline (3.90 mL, 43.17 mmol) and 10 drops of conc. HCl. The resulting solution was heated to 80° C. for 2-3 h. The reaction mass was cooled to room temperature, poured onto ice-cold water and then extracted with EtOAc (3×250 mL). The combined organic phase was washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The crude residue was then purified over silica gel (100-200 M, 2% EtOAc-hexane) to obtain the desired product ii (4.90 g, 39%). 1H-NMR (400 MHz, DMSO-d6): δ 9.72 (br s, 1H), 8.66 (s, 1H), 7.28-7.49 (m, 5H), 6.77 (s, 1H), 4.35 (q, J=7.20 Hz, 2H), 1.34 (t, J=7.20 Hz, 3H). [M+H]+ m/z=277.17.

1. customwas obtained
2. temperatureThe reaction mass was cooled to room temperature
3. additionpoured onto ice-cold water
4. extractionextracted with EtOAc (3×250 mL)
5. washThe combined organic phase was washed with brine
6. dry with materialdried (Na2SO4)
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customThe crude residue was then purified over silica gel (100-200 M, 2% EtOAc-hexane)