Acetic Acid → 4-(3-Dimethylamino-prop-1-ynyl)-3-trifluoromethyl-phenylamine

Participants

Reaction Conditions

Reaction Steps

A mixture of dimethyl-[3-(4-nitro-2-trifluoromethyl-phenyl)-prop-2-ynyl]-amine (2.0 g, 7.4 mmol), iron powder (1.65 g, 29.4 mmol, 4 equiv), AcOH (5 mL), H2O (10 mL), and EtOH (40 mL) is stirred for 30 min at 80° C. The reaction mixture is allowed to cool to rt, basified by addition of a 1 M aqueous solution of NH3, and filtered through Celite. The filtrate is partially concentrated and extracted with EtOAc. The organic phase is washed with brine, dried (Na2SO4), filtered and concentrated. The residue is purified by silica gel column chromatography (CH2Cl2/NH3 (2 N in MeOH), 95:5) to provide the title compound as a brown oil: ES-MS: 243.0 [M+H]+; single peak at tR=2.49 min (System 1); Rf=0.10 (CH2Cl2/NH3 (2 N in MeOH), 95:5).

Provenance & Evidence