Sodium Hydroxide → 3-(4-chlorophenyl)-2-(1H-indol-5-yl)quinazolin-4(3H)-one

Participants

Reaction Steps

Zn dust (0.220 g, 3.35 mmol) was added to a solution of (E)-3-(4-chlorophenyl)-2-(3-(2-(dimethylamino)vinyl)-4-nitrophenyl)quinazolin-4(3H)-one in AcOH (15 mL). After heating and stirring at reflux temperature for 4 hours, the mixture was basified with 1N NaOH and extracted with EtOAc. The organics were washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel, eluting with 20% to 90% EtOAc in heptane, afford the title compound as a white solid (0.048 g, 39%). 1H-NMR (300 MHz, DMSO-d6): δ11.19 (s, 1H), 8.18-8.21 (m, 1H), 7.88-8.00 (m, 1H), 7.75 (d, J=7.7 Hz, 1H), 7.47-7.70 (m, 2H), 7.30-7.44 (m, 5H), 7.20 (d, J=8.4 Hz, 1H), 7.06 (d, J=6.8 Hz, 1H), 6.40 (d, J=2.0 Hz, 1H). MS (APCI) m/z: 372 (M+H)+.

Provenance & Evidence