Water → 2-(4-((6-Bromo-3-nitroquinolin-4-yl)amino)phenyl)-2-methylpropanenitrile

Participants

Reaction Steps

6-Bromo-4-chloro-3-nitroquinoline (Compound of Preparation A, 18 g, 62.6 mmol) and 2-(4-aminophenyl)-2-methylpropanenitrile (Compound of Preparation B, 11 g, 68.9 mmol) was dissolved in acetic acid (350 mL) and the mixture was stirred for 2 hours. Water was added and the yellow precipitate was filtered off. The precipitate was washed with water, saturated aqueous NaHCO3 and water. The yellow solid was dried to obtain the title compound. Yield: 19 g (74%); 1H NMR (DMSO-d6, 300 MHz): δ 10.0 (s, 1H), 8.979 (s, 1H), 8.594 (s, 1H), 7.894-7.926 (d, 1H, J=9.6 Hz), 7.817-7.847 (d, 1H, J=9 Hz), 7.348-7.376 (d, 2H, J=8.4 Hz), 7.011-7.039 (d, 2H, J=8.4 Hz), 1.575 (s, 6H); MS: m/z 409 (M−).

Provenance & Evidence