CID 6432229 → 6-nitro-2,3-dihydro-1H-inden-5-amine

Participants

Reaction Steps

A suspension of the mixture of acetamides 17 and 18 in EtOH (400 mL) and cHCl (180 mL) was stirred at 80° C. for 6 h. The resulting solution was cooled and diluted with water (400 mL) and allowed to stand for 16 h. The precipitate was filtered, washed with water, and air-dried to give amine 2 (27.52 g, 73%, from 16) as an orange powder: mp 129-131° C. [lit. (Schroeder, E.; et al., European J. Med. Chem. 1982, 17, 35) mp (EtOH) 128.5-129.5° C.]; 1H NMR δ 7.93 (s, 1H, H-7), 6.55 (s, 1H, H-4), 5.99 (br s, 2H, NH2), 2.79-2.88 (m, 4H, H-1, H-3), 2.02-2.10 (m, 2H, H-2); 13C NMR δ 154.3, 144.2, 134.0, 131.3, 120.8, 113.5, 33.0, 31.4, 25.7.

Provenance & Evidence