2-[3-(Methyloxy)-4-nitrophenyl]-5-(1-pyrrolidinylmethyl)-1,3,4-oxadiazole → 2-(Methyloxy)-4-[5-(1-pyrrolidinylmethyl)-1,3,4-oxadiazol-2-yl]aniline

Participants

Reaction Steps

A mixture of 2-[3-(methyloxy)-4-nitrophenyl]-5-(1-pyrrolidinylmethyl)-1,3,4-oxadiazole (1.13 g, 3.70 mmol) and platinum on carbon (sulfided) in EtOAc (25 mL) was stirred under H2 (1 atm.) overnight. The mixture was filtered through Celite® and concentrated. Purification by flash chromatography provided the title compound of step B (0.26 g, 0.93 mmol, 25%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.62-1.71 (m, 4H), 2.48-2.57 (m, 4H), 3.76-3.85 (m, 5H), 5.51 (br. s., 2H), 6.64-6.71 (m, 1H), 7.25 (d, J=1.8 Hz, 1H), 7.29 (dt, J=8.1, 2.4 Hz, 1H).

Provenance & Evidence