3,4-Dichloroaniline → HCID 178516418, compound

Participants

Reaction Steps

2,4-quinolinediol (10.0 g, 62.1 mmol) and 3,4-dichloroaniline (13.1 g, 80.7 mmol) were heated to 190° C. in 25 mL NMP for 48 h. After heating was discontinued, solids began to precipitate. These were collected, treated with 8.5 mL of HCl in isopropanol and sonicated in a 4:1 mixture of acetone:isopropanol. After 2.5 h of sonication, the solids were collected. The sonication cycle was repeated to afford 6.79 g of material (19.9 mmol, 32%). 1H NMR (300 MHz, DMSO): 12.7 (s,1 H), 9.34 (s, 1 H), 8.41 (d, 1 H, J=9 Hz), 7.71 (m, 3 H), 7.6 (d, 1 H, J=8.1 Hz), 7.44 (m, 2 H), 6.25 (s, 1 H), 6.08 (broad s, 1 H).

Provenance & Evidence