4-Methoxybenzylamine → Ethyl 8-bromo-4-((4-methoxybenzyl)amino)quinoline-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 8-bromo-4-chloroquinoline-3-carboxylate (1.8 g, 5.72 mmol) in DMF (10 mL) were added p-methoxybenzyl amine (860 mg, 6.27 mmol) and DIPEA (2.22 g, 17.21 mmol) and the reaction mixture was heated at 120° C. for 4 h. Then the reaction mixture was quenched with water and was extracted with EtOAc. The organic layer was washed with brine, separated, dried, filtered and concentrated. The residue was purified by column chromatography to afford 1.2 g of the title product. 1H NMR (300 MHz, DMSO d6): δ 9.11 (br s, 1H), 8.89 (s, 1H), 8.46-8.43 (d, J=8.7 Hz, 1H), 8.12-8.09 (d, J=7.8 Hz, 1H), 7.38-7.33 (t, J=8.4 Hz, 1H), 7.27-7.24 (d, J=8.4 Hz, 2H), 6.91-6.89 (d, J=8.1 Hz, 2H), 8.17 (d, 2H), 4.26-4.24 (q, J=7.2, 14.1 Hz, 2H), 3.72 (s, 3H), 1.29-1.24 (t, J=6.9 Hz, 3H).

Provenance & Evidence