2,4-Dimethoxybenzylamine → 2-[(2,4-Dimethoxyphenyl)methyl]-6-nitroisoquinolin-1(2H)-imine

Participants

Reaction Steps

Intermediate 1A (4.6 g, 21.2 mmol) and 2,4-dimethoxylbenzylamine (4.0 mL, 1.25 eq) in DMPU (10 mL) was heated at 140° C. for 3 h. The solvent was removed by vacuum distillation and residue treated with hexanes/EtOAc (1:1). The solid was collected by filtration and washed with hexane to give Intermediate 1B (4.6 g, 64%). 1H NMR (400 MHz, DMSO-d6) δ 3.72 (s, 3H), 3.81 (s, 3H), 4.96 (s, 1H), 6.28 (d, J=6.6 Hz, 1H), 6.46 (d, J=7.5 Hz, 1H), 6.58 (d, J=1.8 Hz, 1H), 7.03 (d, J=8.8 Hz, 1H), 7.27 (d, J=6.2 Hz, 1H), 8.02 (dd, J=9.0, 2.4 Hz, 1H), 8.31 (d, J=2.2 Hz, 1H), 8.43 (d, J=8.4 Hz, 1H).

Provenance & Evidence