Phosphorus oxychloride → HCID 59857985, compound

Participants

Reaction Steps

A mixture of 7-fluoro-8-methoxy-2-quinolinol (4a) (2.26 g, 11.7 mmol) and POCl3 (5.5 mL, 60 mmol) was refluxed for 1.5 hours. The contents were concentrated and neutralized with NaHCO3 and the mixture heated with water and AcOEt. The solution was filtered to remove undissolved impurities, followed by extraction. The organic layer was washed with saturated NaCl and dried with MgSO4. The product was recrystallized from ***CHCl3-hexanes, which yielded white crystals (2.24 g, 90% yield): mp 85-86° C.; 1H NMR (400 MHz, CDCl3) 8.06 (d, J=8.8 Hz, 1H) 7.48 (dd, J=8.8, 5.6 Hz, 1H), 7.37 (d, J=8.8 Hz, 1H), 7.35 (dd, J=9.2, 2.4 Hz, 1H), 4.23 (d, J=2.4 Hz, 3H). 19F NMR (376 MHz, CHCl3) −127.35 (dd, J=10.9, 2.6 Hz).

Provenance & Evidence