Toluene → HCID 86586049, compound

Participants

Reaction Steps

A solution of toluene (8 mL), piperidine (0.008 mL), acetic acid (0.009 mL) and 6-[3-(3-pyridyl)-4,5-methylenedioxyphenyl]-2-naphthaldehyde (0.304 g, 0.86 mmol) and 2,4-thiazolidinedione (101 mg, 0.86 mmol) was heated at reflux for 16 hours under an argon atmosphere. The resulting suspension was filtered and the solid was stirred at room temperature in EtOH. After 1 hours, the solid was filtered and dried under high vacuum to afford 78.0 mg of 6-[3-(3-pyridyl)-4,5-methylenedioxyphenyl]-naphthalen-2-yl-methylene-2,4-thiazolidinedione, mp 298–300° C. 1H NMR (300 MHz, DMSO-d6): δ 6.16 (s, 2H), 7.10–7.28 (m, 4H), 7.51 (dt, J1=8.0 Hz, J2=1.5 Hz, 1H), 7.66 (dd, J1=8.4 Hz, J2=1.8 Hz, 1H), 7.75–7.85 (m, 2H), 7.90 (s, 1H), 7.93 (d, J=8.7 Hz, 1H), 8.11 (s, 1H), 8.25 (d, J=1.5 Hz, 1H), 8.34 (dd, J1=4.8 Hz, J2=1.4 Hz, 1H), 12.69 (brs, 1H).

Provenance & Evidence