Azobisisobutyronitrile → 7-Quinolinemethanol

Participants

Reaction Steps

To a solution of 7-methylquinoline (2.86 g) in ethyl acetate (100 mL) were added N-bromosuccinimide (3.56 g) and 2,2′-azobis(isobutyronitrile) (197 mg) at room temperature, and the mixture was refluxed for 1.5 hr. The reaction mixture was allowed to cool to room temperature, and washed with water. The obtained organic layer was concentrated under reduced pressure, to the residue were added DME (200 mL), water (100 mL), and silver carbonate (27.6 g), and the mixture was stirred at room temperature for 20 hr. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/methanol), and then purified by NH silica gel column chromatography (ethyl acetate/hexane) to give the title compound (94 mg).

Provenance & Evidence