4-Nitroquinoline 1-Oxide → 4-Aminoquinoline

Participants

Reaction Conditions

Reaction Steps

A suspension of 4-nitroquinoline N-oxide (10 g, 52.5 mmol) and metal iron (26.4 g, 0.47 mol) in acetic acid (500 ml) was stirred under heating at 110° C. for 3 hr. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. To the residue was added an aqueous sodium hydroxide solution to make the solution alkaline, which was followed by extraction with chloroform (50 ml×6). The organic layer was washed with water and saturated brine, dried over sodium sulfate and concentrated under reduced pressure to give 4-aminoquinoline (6.0 g, 79%, brown crystals).

Provenance & Evidence