Phosphorus trichloride → 2-Chloroquinoline

Participants

Reaction Steps

To 13.25 g (69.7 mmol) of 4-hydroxy-3-nitroisoquinoline was added 120 mL of phosphorous trichloride. After the mixture had been refluxed for 3 hours, 80 mL of POCl3 was distilled out. The remaining solution was poured onto approximately 150 g of crushed ice. The resulting solid was filtered and recrystallized from ethanol to give 6.2 g (42.5%) of the chioroquinoline as yellow needles: mp 103-104° C. (lit mp 108-109° C.); 1H-NMR (DMSO-d6, 200 MHz) δ 9.20 (s, 1H), 8.5 (d, 1H) 8.30 (d, 1H), 7.8 (m, 2H); IR (KBr) 1530 (s, NO2), 1344 (s, NO2) cm−1.

Provenance & Evidence