Hydrochloric Acid → 2-(4-Methoxy-2-methylphenyl)-ethylamine hydrochloride

Participants

Reaction Steps

4-Methoxy-2-methylphenylacetonitrile (3.0 g, 18.6 mmol) was dissolved in absolute denatured ethyl alcohol (65 mL). To the solution was added conc. HCl (2.4 mL) and 10% Pd/C (300 mg). The suspension was deaerated in a 500 mL Parr hydrogenation bottle, then pressurized with 55 pounds per square inch (psi) hydrogen (H2) and shaken. After 20 h, the reaction was recharged with H2 and 10% Pd/C. After a total of 96 h, the reaction mixture was filtered through Celite and the filtrate was concentrated in vacuo. The off-white solid residue was recrystallized from isopropyl alcohol and collected by suction filtration to afford 2-(4-methoxy-2-methylphenyl)-ethylamine hydrochloride (1.86 g, 50%) as a white solid, mp 220-222° C. (gradual softening and discoloration from 104-220° C.). The filtrate was concentrated in vacuo and the residue was washed with EtOAc and filtered, providing an additional 1.34 g for a total yield of 3.2 g (85%): 1H NMR (DMSO-d6) 8.25 (br s, 3H), 7.09 (d, 1H), 6.75 (m, 2H), 3.71 (s, 3H), 2.87 (m, 4H), 2.27 (s, 3H); GC-MS m/z 165 ([M−Cl]+).

Provenance & Evidence