4-Chloro-8-nitroquinoline → 8-Aminoquinoline

Participants

Reaction Steps

To a solution of 4-chloro-8-nitroquinoline (Intermediate-11, step-2, 150 mg, 0.71 mmol) in EtOAc (3 mL) was added 10% Pd on C (75 mg) and the suspension was hydrogenated in a Parr apparatus for 4 h at 20 psi. Then the reaction mixture was filtered through celite and the filtrate was concentrated. The residue was purified by column chromatography using 10% EtOAc in CHCl3 to afford 50 mg of the title product. 1H NMR (300 MHz, DMSO d6): δ 8.71 (d, 1H), 8.17 (d, J=8.4 Hz, 1H), 7.47-7.43 (m, 1H), 7.28 (t, J=7.8 Hz, 1H), 7.05 (d, J=8.4 Hz, 1H), 6.86 (d, J=7.2 Hz, 1H), 5.90 (s, 2H).

Provenance & Evidence