反应详情

To a slurry of ethyl 2-(7-((3-chlorobenzyl)oxy)-2-oxo-1,2-dihydroquinolin-3-yl)acetate (31.4 g, 0.08 mol) in chloroform (314 mL) at ambient temperature was added oxalyl dichloride (21.7 mL, 0.25 mol) and DMF (0.66 mL, 0.01 mol). The resulting slurry was heated to reflux for 1 h. The reaction was quenched with sat. aqueous NaHCO3 (400 mL). The aqueous layer was extracted with DCM (2×200 mL) and the combined organic layers were washed with brine and dried over Na2SO4. The organic layer was concentrated under reduced pressure to furnish a black solid that was triturated in 1:1 EtOAc:hexanes (400 mL) and filtered. The solid was recrystallized from MeOH to furnish (17.0 g, 52%). Two additional crops of product were acquired from the mother liquor to furnish a total of 27.8 g (84.3%) of the title compound. 1H NMR (400 MHz, DMSO-d6) δ 8.34 (s, 1H), 7.93 (d, J=9.0 Hz, 1H), 7.59 (s, 1H), 7.51-7.37 (m, 5H), 5.31 (s, 2H), 4.13 (q, J=7.1 Hz, 2H), 3.94 (s, 2H), 1.19 (t, J=7.1 Hz, 3H). [M+H]=390.2

1. temperatureThe resulting slurry was heated
2. temperatureto reflux for 1 h
3. customThe reaction was quenched with sat. aqueous NaHCO3 (400 mL)
4. extractionThe aqueous layer was extracted with DCM (2×200 mL)
5. washthe combined organic layers were washed with brine
6. dry with materialdried over Na2SO4
7. concentrationThe organic layer was concentrated under reduced pressure
8. customto furnish a black solid
9. customthat was triturated in 1:1 EtOAc
10. filtrationhexanes (400 mL) and filtered
11. customThe solid was recrystallized from MeOH
12. customto furnish (17.0 g, 52%)