反应详情

To a stirred solution of N,N-dimethyl-3-(6-nitro-3,4-dihydroquinolin-1(2H)-yl)propan-1-amine (1 g, 3.80 mmol) in dichloromethane (20 ml) was added phenyl carbonochloridate (0.715 ml, 5.70 mmol). The resulting solution was stirred at room temperature overnight. The reaction mixture was then diluted with water and extracted with dichloromethane (3×). The combined organics were dried, filtered and concentrated, then chromatographed in 50-100% ethyl acetate in hexanes, giving the desired phenyl methyl(3-(6-nitro-3,4-dihydroquinolin-1(2H)-yl)propyl)carbamate (1.02 g, 2.76 mmol, 72.7% yield). 1H NMR (DMSO-d6) δ 7.88 (t, J=7 Hz, 1H), 7.78 (s, 1H), 7.37 (t, J=7 Hz, 2H), 7.20 (t, J=7 Hz, 1H), 7.12-7.06 (m, 2H), 6.70 (d, J=9 Hz, 1H), 3.50-3.33 (m, 6H), 3.06, 2.93 (2s, 3H), 2.76-2.71 (m, 2H), 1.92-1.81 (m, 4H). ESI-MS (m/z, %) 370 (MH+, 100).

1. extractionextracted with dichloromethane (3×)
2. customThe combined organics were dried
3. filtrationfiltered
4. concentrationconcentrated
5. customchromatographed in 50-100% ethyl acetate in hexanes