4-Methoxybenzylamine → HCID 59184872, compound

Participants

Reaction Steps

A mixture of 3,5-difluoro-benzonitrile (2.78 g, 20 mmol) and p-methoxybenzyl amine (5.74 ml, 44 mmol) in DMSO (20 ml) was stirred for 8 hr. in an oil bath (100-110° C.). After cooling to room temperature, the mixture was diluted with ether, washed with water, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo. The residue was purified by silica gel column chromatography (eluent, EA: hexane (from 1:13 to 1:10)) to afford 3.92 g (76%) of a white solid. m.p. 93-94° C.; 1H NMR (200 MHz, CDCl3) δ 3.61 (3H, s), 4.04 (2H, s); 4.16 (1H, br. s), 6.27 (1H, m), 6.42-6.47 (2H, m), 6.69 (2H, d, J=7.2 Hz), 7.06 (2H, d, J=7.2 Hz).

Provenance & Evidence