Phosphoric Acid → HCID 5008364, compound

Participants

Reaction Conditions

Reaction Steps

3-Methoxyphenylethylamine (1.51 g) and 2,4-dimethylbenzaldehyde (1.34 g) were mixed together. Phosphoric acid, 85%, (20 mL) was added then the reaction was warmed to 37° C. for 60 h. The reaction was cooled, poured into water (300 mL) then washed with diethyl ether (2×50 mL). The aqueous layer was diluted to 700 mL with water, made basic (pH=10) by the slow addition of sodium hydroxide, and then extracted with diethyl ether (2×150 mL). The organic extracts were dried and evaporated. The resulting residue was purified by silica gel chromatography (eluant: ethyl acetate-hexane, gradient from 1:1 to 100% ethyl acetate) to give the title compound (1.458 g). MS: 268.2 (MH+); HPLC tR: 1.71 min (method D); TLC Rf: 0.21 (ethyl acetate); 1H NMR (DMSO-d6): 6.96 (s, 1H), 6.86 (s, 2H), 6.67 (d, 1H, J=2.3 Hz), 6.59 (dd, 1H, J=2.5, 8.5 Hz), 6.44 (d, 1H, J=8.5 Hz), 5.07 (s, 1H), 3.69 (s, 3H), 3.03-3.11 (m, 1H), 2.82-2.89 (m, 2H), 2.63-2.77 (m, 1H), 2.26 (s, 3H), 2.23 (s, 3H).

Provenance & Evidence