Hydrazine → HCID 68328171, compound

Participants

Reaction Steps

To a suspension of Raney-Ni (100 mg) in MeOH (2 mL) was added N-isopropyl-5-(3-nitro-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine (200 mg, 0.698 mmol) followed by addition of NH2NH2 (0.2 mL). The reaction mixture was stirred at RT for 1 h. The mixture was then filtered through a plug of Celite and the filtrate was concentrated. The residue was treated with water and the resulting suspension was filtered, washed with water and dried. The crude product was purified by washing with petroleum ether (2×5 mL) to afford 5-(3-amino-1H-indol-5-yl)-N-isopropyl-1,3,4-oxadiazol-2-amine (50 mg, 27%) as a brown solid. MS (ESI, pos. ion) m/z: 258.2 (M+1); 1H-NMR (400 MHz, DMSO-d6): δ 10.43 (s, 1H), 8.02 (s, 1H), 7.46-7.49 (m, 2H), 7.30 (d, 1H, J=8.4 Hz), 6.67 (brs, 1H), 4.27 (s, 2H), 3.70-3.76 (m, 1H), 1.23 (d, 6H, J=6.4 Hz).

Provenance & Evidence