Hydroxyamine hydrochloride → (1E)-11-(3-fluorophenyl)-1-hydroxyimino-9-methoxy-3,4-dihydro-2H-benzo[b]quinolizin-6-one

Participants

Reaction Steps

To a solution of 11-(3-fluorophenyl)-9-methoxy-3,4-dihydro-2H-pyrido[1,2-b]isoquinoline-1,6-dione (125 mg) in 4 mL pyridine was added hydroxylamine hydrochloride (51 mg). The reaction was heated to reflux for 5 h, then cooled to room temp and partitioned between ether and water. The aqueous solution was extracted with ether (2×). The combined organic solutions were washed with 1 N HCl (1×), and 10% bicarb (1×), then dried (MgSO4) and concentrated. Flash chromatography (10-70% EtOAc/hexanes) gave the titled compound.

Provenance & Evidence