Phosphorus oxychloride → 4-Chloroquinoline

Participants

Reaction Steps

A solution of 4-quinolinol (1.0 g, 6.88 mmol) in POCl3 (3 mL) was heated at reflux for 2 h. Then the reaction mixture was concentrated and the concentrate was dissolved in EtOAc. The organic layer was washed with a saturated solution of NaHCO3 and water. The organic layer was separated, dried, filtered and concentrated to afford 1.1 g of the title product. 1H NMR (300 MHz, DMSO d6): δ 8.87 (d, J=4.5 Hz, 1H), 8.23 (d, J=7.8 Hz, 1H), 8.14-8.11 (d, J=8.7 Hz, 1H), 7.93-7.88 (t, J=7.5 Hz, 1H), 7.82-7.77 (m, 2H).

Provenance & Evidence