Sodium hydride → HCID 43446516, compound

Temperature

0 °C

To a stirred solution of 6-nitro-3,4-dihydroquinolin-2(1H)-one (2 g, 10.41 mmol) at 0° C. under argon was added sodium hydride, 60% (0.624 g, 15.61 mmol). The mixture was stirred at 0° C. until bubbling ceased, approximately 30 min. To this mixture was then added 1-chloro-3-iodopropane (3.29 ml, 31.2 mmol). The mixture was then allowed to warm slowly to room temperature and stirred overnight. The reaction mixture was then diluted with water and extracted with ethyl acetate (2×). The combined organics were then washed with a 1:1 mixture of water and brine (3×) then brine (1×). The organic phase was then dried, filtered and concentrated on to silica gel, then chromatographed in 10-50% ethyl acetate in hexanes, giving the desired 1-(3-chloropropyl)-6-nitro-3,4-dihydroquinolin-2(1H)-one (2.05 g, 7.63 mmol, 73.3% yield) as a yellow solid. 1H NMR (DMSO-d6) δ 8.15 (m, 1H), 8.13 (dd, J=9, 2.7 Hz, 1H), 7.36 (d, J=9 Hz, 1H), 4.07 (t, J=7.4 Hz, 2H), 3.71 (t, J=6.5 Hz, 2H), 3.02 (t, J=7.4 Hz, 2H), 2.63 (t, J=7.4 Hz, 2H), 1.99 (quint, J=7.2 Hz, 2H).

1. customuntil bubbling
2. temperatureto warm slowly to room temperature
3. stirringstirred overnight
4. extractionextracted with ethyl acetate (2×)
5. washThe combined organics were then washed with a 1:1 mixture of water and brine (3×)
6. customThe organic phase was then dried
7. filtrationfiltered
8. concentrationconcentrated on to silica gel
9. customchromatographed in 10-50% ethyl acetate in hexanes

ORD record

ord-64690f1995ab413cb6c8c4d51d5992da

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08173813B2