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

Participants

Reaction Steps

(E)-2-(2-(Dimethylamino)vinyl)-4-nitrobenzonitrile (4.6 g, 21.2 mmol) and 2,4-dimethoxylbenzylamine (4.0 mL, 1.25 equiv) in DMPU (10 mL) were heated at 140° C. for 3 h. The solvent was removed by vacuum distillation and residue was treated with hexanes/ethyl acetate (1:1). The solid was collected by filtration and washed with hexane to give 2-(2,4-dimethoxybenzyl)-6-nitroisoquinolin-1 (2H)-imine (4.6 g). 1H NMR (400 MHz, DMSO-d6) δ ppm 3.72 (s, 3 H) 3.81 (s, 3 H) 4.96 (s, 1 H) 6.28 (d, J=6.59 Hz, 1 H) 6.46 (d, J=7.47 Hz, 1 H) 6.58 (d, J=1.76 Hz, 1 H) 7.03 (d, J=8.79 Hz, 1 H) 7.27 (d, J=6.15 Hz, 1 H) 8.02 (dd, J=9.01, 2.42 Hz, 1 H) 8.31 (d, J=2.20 Hz, 1 H) 8.43 (d, J=8.35 Hz, 1 H).

Provenance & Evidence