Tetrahydrofuran → 8-Fluoro-6-nitro-1,2,3,4-tetrahydroquinoline

Participants

Reaction Conditions

Reaction Steps

8-Fluoro-6-nitro-3,4-dihydroquinolin-2(1H)-one (5.9 g, 28.1 mmol) was stirred in borane-THF complex, 1M in THF (140 ml, 140 mmol). The solution was heated to 60° C. and stirred overnight. The mixture was then cooled in an ice bath and quenched via addition of methanol (30 mL). The quenched solution was concentrated, then dissolved in methanol and refluxed for 1 h. The solution was then concentrated onto silica gel and chromatographed using 5-30% ethyl acetate in hexanes to give the desired 8-fluoro-6-nitro-1,2,3,4-tetrahydroquinoline (4.34 g, 22.12 mmol, 79% yield). 1H NMR (DMSO-d6) δ 7.77-7.71 (m, 1H), 7.73 (m, 1H), 7.31 (brs, 1H), 3.35-3.28 (m, 2H), 2.77 (t, J=6.2 Hz, 2H), 1.85-1.77 (m, 2H).

Provenance & Evidence