反应详情

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)+.

1. extractionextracted with EtOAc (2×30 mL)
2. extractionThe organic extract
3. washwas washed with saturated NaCl (5 mL)
4. dry with materialdried over Na2SO4
5. filtrationThe solution was filtered
6. concentrationconcentrated in vacuo
7. customto give the crude material as a light-yellow oil
8. customThe crude product was purified by silica gel chromatography
9. washeluting with 80% EtOAc/hexanes