Triethylamine → 9-amino-1-methyl-5,6-dihydro-1H-[1,2,4]triazino[4,3-a]quinolin-2(3H)-one

Participants

Reaction Steps

To a solution of 9-(2,5-dimethyl-1H-pyrrol-1-yl)-1-methyl-5,6-dihydro-1H-[1,2,4]triazino[4,3-a]quinolin-2(3H)-one (0.140 g, 0.45 mmol) and triethylamine (0.138 g, 1.362 mmol) in EtOH (9 mL) was added a solution of hydroxylamine hydrochloride (0.095 g, 1.362 mmol) in water (3 mL) and the reaction mixture was heated to reflux for 3 h. The reaction mixture was cooled to ambient temperature and the solvent was removed in vacuo. The residue was purified by column chromatography on silica gel (eluting with 50-100% EtOAc in petroleum ether) to give 9-amino-1-methyl-5,6-dihydro-1H-[1,2,4]-triazino[4,3-a]quinolin-2(3H)-one (0.070 g, 67%). 1H NMR (CDCl3, 400 MHz): δ 8.06 (brs, 1H), 6.91 (d, J=8.0 Hz, 1H), 6.31 (d, J=8.0 HZ, 1H), 6.26 (s, 1H), 4.60 (q, J=6.8 HZ, 1H), 3.63 (brs, 2H), 2.67 (m, 2H), 2.53 (m, 2H), 1.42 (d, J=6.8 Hz, 3H).

Provenance & Evidence