Ethanol → HCID 71744029, compound

Participants

Reaction Steps

To a flask containing 8-bromo-6-nitroquinoline (2.05 g, 8.1 mmol), electrolytic iron (2.26 g, 40.5 mmol) and ammonium chloride (2.25 g, 42.1 mmol) was added ethanol (20 ml) and water (10 ml). The flask was fitted with an efficient reflux condenser and then heated to near reflux (oil bath) for 3 hours. The hot material was then filtered through a plug of celite and rinsed well with hot methanol (100 ml). The solvent was removed. The residue was taken up in ethyl acetate (60 ml) and water (60 ml) and transferred to a separatory funnel, agitated and the organic phase collected. The organic phase was washed with an equal volume of brine. The aqueous phases were back extracted with ethyl acetate (2×50 ml). The combined ethyl acetate extracts were dried over MgSO4, and concentrated in vacuo. The resulting residue was crystallized from hot dichloromethane/hexanes to provide the desired product as a brown powder (860 mg).

Provenance & Evidence