Tetrahydrofuran → HCID 59807100, compound

Participants

Reaction Conditions

Reaction Steps

1-(3-((2-Hydroxyethyl)(methyl)amino)propyl)-6-nitro-3,4-dihydroquinolin-2(1H)-one (200 mg, 0.651 mmol) was stirred in borane-tetrahydrofuran complex, 1M sol'n in THF (6.507 mL, 6.51 mmol) until the material dissolved. The resulting solution was then heated at 60° C. overnight. The reaction mixture was then cooled in an ice bath and quenched with methanol (slowly). The solution was then concentrated, redissolved in methanol (5 mL) and stirred with 1M HCl (5 mL) at reflux for 1 h. The mixture was then basified with 1M NaOH and extracted with dichloromethane (3×). The combined organics were dried, filtered and concentrated, then chromatographed on silica gel eluting with ethyl acetate, followed by 5% (2M NH3/methanol) in dichloromethane. 1H NMR (DMSO-d6) δ 7.88 (dd, J=9.3, 2.7 Hz, 1H), 7.77 (d, J=2.7 Hz, 1H), 6.72 (d, J=9.3 Hz, 1H), 4.40 (t, J=5.4 Hz, 1H), 3.51-3.32 (m, 6H), 2.74 (t, J=6 Hz, 2H), 2.41-2.33 (m, 4H), 1.89-1.81 (m, 2H), 1.72-1.64 (m, 2H).

Provenance & Evidence