4-Methyl-5-(3-nitrophenyl)-1,3-oxazole → 3-(4-Methyl-1,3-oxazol-5-yl)aniline

Participants

Reaction Steps

Pd/C (5 g) was transferred carefully to a solution of 4-methyl-5-(3-nitrophenyl)-1,3-oxazole (50 g) in MeOH (600 mL) in a Parr-shaker bottle and hydrogenated at 3.5 kg pressure for 20 h. The reaction mixture was filtered over a celite bed and the filtrate concentrated. The residue was purified by silica gel column chromatograph using 40% EtOAc in petroleum-ether to get a yellow solid. Yield 18 g (42%). 1H NMR (400 MHz, DMSO-d6) δ 8.23 (s, 1H), 7.08 (t, J=8.0 Hz, 1H), 6.82 (s, 1H), 6.71 (d, J=7.9 Hz, 1H), 6.52 (d, J=8.2 Hz, 1H), 5.24 (s, 2H), 2.29 (s, 3H).

Provenance & Evidence