3-Nitroquinolin-4-amine → 3,4-Diaminoquinoline

Participants

Reaction Steps

Compound 8 was prepared as described elsewhere [Van Galen, P. J. M. et. al. (1991) ibid.]. In brief, to a mixture of 3-nitro-4-aminoquinoline 7 (3.2 g, 20 mmol) in absolute ethanol (60 ml) was added 10% palladium on charcoal (0.17 g). The mixture was hydrogenated under 2.5-3.5 atm pressure till the product was formed and subsequently filtered over Hyflo. The filtrate was evaporated and the residue was gradually solidified and dried in vacuum. Yield: 2.66 g (98%). Mp.: 183-185° C. MS (ESI) m/z 161.0 (M+1)+. 1H NMR (DMSO-d6): δ 4.73 (broad s, 2H, NH2); 5.88 (s, 2H, NH2); 7.16-7.37 (m, 2H, Ar); 7.64-7.70 (m, 1H, Ar); 7.98-8.03 (m, 1H, Ar); 8.22 (s, 1H, Ar).

Provenance & Evidence