4-[5-(4-Chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-2-nitro-phenylamine → 4-[5-(4-Chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-benzene-1,2-diamine

Participants

Reaction Steps

To a 25 mL rbf was added 0.4137 g (1.31 mmol) of 4-[5-(4-Chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-2-nitro-phenylamine, 4 mL of THF/EtOH (1:1). Vacuum flushed 3×, then added 0.1655 g of PtO2 (40% by weight) as a slurry in 2 mL of THF/EtOH (1:1). Flushed with H2 3×. Allowed to stir at r.t. for 18 h. Added 10 ml DCM, and Celite let stir 1 h, then filtered over Celite pad, and rinsed with 20 mL DCM. Reduced in vacuo to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 4.85 (br. s., 1.7 H) 5.31 (br. s., 1.7 H) 6.62 (d, J=8.08 Hz, 1 H) 7.19 (dd, J=8.08, 1.89 Hz, 1 H) 7.26 (d, J=2.02 Hz, 1 H) 7.66-7.70 (m, 2 H) 8.02-8.06 (m, 2 H). MS (m/z) 287.2 M (+1), tR=1.18, Meth 10

Provenance & Evidence