Benzaldehyde → HCID 22395292, compound

Participants

Reaction Steps

A mixture of 4-aminoquinaldine (2-methyl4-quinolinamine) (3.00 g, 19.0 mmol), benzaldehyde (6.05 g, 5.80 mL, 57.0 mmol) and acetic anhydride (5.82 g, 5.38 mL, 57.0 mmol) was stirred at reflux for 5 h. After cooling, the volume was reduced in vacuo to give a brown oil, which was triturated overnight with diethyl ether. A formed solid was collected by filtration and air-dried to provide the title compound as a yellow solid (3.52 g, 64%). MS (API+): M+1: 289 (100%); 1H NMR (300 MHz, DMSO-d6) d 2.30 (s, 3H), 7.32-7.51 (m, 4H), 7.55-7.65 (m, 1H), 7.70-7.80 (m, 4H), 8.00 (d, J=7.7 Hz, 1H), 8.32 (d, J=8.1 Hz, 1H), 8.38 (s, 1H), 10.24 (s, 1H, exchangeable).

Provenance & Evidence