N,N-dimethyl-2-(3-nitro-5-(trifluoromethyl)phenoxy)ethanamine → 3-[2-(Dimethylamino)ethoxy]-5-(trifluoromethyl)aniline

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Reaction Steps

A suspension of N,N-dimethyl-2-(3-nitro-5-(trifluoromethyl)phenoxy)ethanamine (75 mg, 0.270 mmol) in MeOH (5 mL) was added to a solution of Pd/C (57.4 mg, 0.539 mmol) in MeOH (5 mL). The mixture was hydrogenated at 26° C. for 3 h under a H2 atmosphere. Then the solution was filtered and concentrated to afford 3-(2-(dimethylamino)ethoxy)-5-(trifluoromethyl)aniline (60.3 mg, 0.243 mmol, 90% yield). TLC (PE/EA=1:1, Rf=0.5): 1H NMR (400 MHz, CD3OD) δ 6.56 (s, 1H), 6.48 (s, 2H), 4.24-4.17 (m, 2H), 3.18 (t, J=5.1 Hz, 2H), 2.67 (s, 6H). ES-LCMS m/z 249 (M+H).

Provenance & Evidence