8-Hydroxyquinoline → CID 57672264

Participants

Reaction Steps

To a suspension of 7-chloro-1-oxo-2-[4-(trifluoromethoxy)benzyl]isoindoline-5-carbonitrile (500 mg, 1.36 mmol) in ethanol (2 ml), 8-hydroxyquinoline (495 mg, 3.41 mmol) was added, followed by a solution of hydroxylamine hydrochloride (199 mg, 2.86 mmol) in water (1 ml) and a solution of sodium carbonate (230 mg, 2.2 mmol) in water (1 ml). The resulting mixture was refluxed for 4 hours. After removal of solvents, the residue was loaded to a flash chromatography. The product was purified (20% EtOAc/hexanes to 2% ammonia in MeOH/EtOAc) and obtained a 500 mg of greenish foam (90%). 1H NMR (300 MHz, CDCl3): δ 10.04 (s, 1H) 7.48-7.61 (m, 2H), 7.28-7.36 (m, 2H), 7.17-7.21 (m, 2H), 6.04 (br, 1H), 4.77 (s, 2H), 4.22 (s, 2H).

Provenance & Evidence