Hydrochloric Acid → 5-Fluoroquinolin-7-amine

Participants

Reaction Steps

A mixture of N-(diphenylmethylene)-5-fluoroquinolin-7-amine (185 mg, 0.566 mmol) and hydrochloric acid (1.132 mL, 1.132 mmol) in THF (5 mL) was stirred at room temperature for 3 h. The reaction mixture was diluted with saturated NaHCO3 (5 mL) and extracted with EtOAc (2×30 mL). The organic extract was washed with saturated NaCl (5 mL) and dried over Na2SO4. The solution was filtered and concentrated in vacuo to give the crude material as a light-yellow oil. The crude product was purified by silica gel chromatography eluting with 80% EtOAc/hexanes to give 5-fluoroquinolin-7-amine (82 mg, 0.506 mmol, 89% yield). 1H NMR (300 MHz, CDCl3) δ 4.02 (s, 2H) 7.11 (dd, J=9.65, 8.18 Hz, 1H) 7.29-7.40 (m, 1H) 7.45 (d, J=2.48 Hz, 1H) 7.76 (d, J=8.48 Hz, 1H) 8.53 (d, J=2.78 Hz, 1H). m/z (ESI, +ve ion) 163.1 (M+H)+.

Provenance & Evidence