6-Nitroquinoline → 6-Aminoquinoline

Participants

Reaction Steps

A suspension of 6-nitro-quinoline (8.7 g, 5 mmol), palladium on charcoal (10%) (0.1 g) in methanol (0.2 L) was hydrogenated at room temperature for 24 with stirring. The catalyst was filtered and the solvent evaporated to yield a yellow solid. Crystallisation from ethyl acetate yielded the pure title compound as a pale yellow solid (3.3 g, 46%). MS m/z: 145 [M+H+]. 1H NMR (270 MHz, CHCl3-d) δ ppm 3.89 (s, 2H) 6.87 (d, J=2.64 Hz, 1H) 7.14 (dd, J=8.97, 2.64 Hz, 1H) 7.25 (dd, J=8.44, 4.22 Hz, 1H) 7.88 (dd, J=7.92, 1.58 Hz, 1H) 7.90 (d, J=8.97 Hz, 1H) 8.63 (dd, J=4.22, 1.58 Hz, 1H).

Provenance & Evidence