Phenyl chloroformate → HCID 59807118, compound

Participants

Reaction Conditions

Reaction Steps

1-(2-(Dimethylamino)ethyl)-6-nitro-3,4-dihydroquinolin-2(1H)-one (1.16 g, 4.40 mmol) was dissolved in dichloromethane (20 mL) in a round bottom flask at room temperature. The solution was cooled to 0° C. and phenyl chloroformate (0.829 mL, 6.61 mmol) was added slowly to avoid an excessive exotherm. The reaction mixture was then warmed to room temperature and stirred overnight. The reaction mixture was then diluted with dichloromethane and quenched with dilute NaOH (˜0.5 M). The aqueous phase was extracted with dichloromethane (3×) and the combined organics were dried over sodium sulfate, filtered and concentrated. The resulting residue was then chromatographed in 50-100% ethyl acetate in hexanes. Yield: 1.29 g, 78%. 1H NMR (CDCl3) δ 8.13 (dd, 1H, J=9.0, 2.7 Hz), 8.05 (t, 1H, J=3.3 Hz), 7.41 (m, 3H); 7.23 (m, 1H); 7.06 (m, 2H), 4.23 (m, 2H), 3.70 and 3.58 (2t, 2H, J=7.2 Hz), 3.19 and 3.09 (2s, 3H), 3.00 (t, 2H, J=7.4 Hz), 2.72 (t, 2H, J=7.4 Hz); ESI-MS (m/z, %): 392 (MNa+, 100), 370 (MH+, 28).

Provenance & Evidence