Pentylamine → HCID 57850035, compound

Participants

Reaction Steps

N-(2-Formyl-3-nitrophenyl)formamide (5a, 20.0 g, 103 mmol) and n-pentylamine (23.9 ml, 206 mmol) were dissolved in EtOH (240 ml) and the mixture stirred at room temperature for 3 h. After the mixture was concentrated under reduced pressure, EtOAc (100 ml) was added to the residue, and the generating yellow crystal was collected by filtration. The crystal was washed with EtOAc and dried under vacuum to obtain 4-hydroxy-5-nitro-3-pentyl-3,4-dihydroquinazoline (6a, 19.6 g, 72%); 1H NMR (270 MHz) δ (CDCl3) 0.91 (t, J=6.7 Hz, 3H), 1.26-1.38 (m, 4H), 1.67-1.78 (m, 2H), 3.21 (dt, J=13.9 and 7.9 Hz, 1H), 3.77 (ddd, J=6.3, 7.6 and 13.9 Hz, 1H), 6.57 (s, 1H), 6.90 (s, 1H), 7.30-7.41 (m, 2H), 7.80 (dd, J=1.7 and 7.6 hz, 1H); MS (ES) m/z 264 (M++1).

Provenance & Evidence