4-(2-(Dimethylamino)ethoxy)-2-nitroaniline → 4-(2-(Dimethylamino)ethoxy)benzene-1,2-diamine

Participants

Reaction Steps

To a Parr hydrogenation bottle was added 3.5 g of 4-(2-(dimethylamino)ethoxy)-2-nitroaniline, 10% palladium in carbon (50% w/w water, 1.0 g) and methanol (100 mL). The atmosphere of the vessel was replaced by hydrogen gas. The reaction was carried out on the Parr shaker at 40 psi at room temperature for 1 hour. The reaction mixture was filtered through a plug of Celite. 2.0 g of sodium bicarbonate was subsequently added to the filtrate, which was stirred for 10 minutes. The filtrate was concentrated reduced pressure and the resulting residue was triturated with diethylether to give 4-(2-(dimethylamino)ethoxy)benzene-1,2-diamine (2.2 g, 73%). 1H-NMR (400 MHz, MeOH-d4): δ 6.67 (d, 1H), 6.44 (d, 1H), 6.27 (dd, 1H), 4.18 (t, 2H), 3.50 (t, 3H), 2.92 (s, 6H). MS (EI): 196 (MH+).

Provenance & Evidence