Hydrochloric Acid → HCID 51347777, compound

Participants

Reaction Steps

To a solution of 1-phenyl-2-o-tolylethanone (Intermediate 9) (100 mg, 0.47 mmol), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (93.8 mg, 0.47 mmol), and urea (84.7 mg, 1.41 mmol) in 20 mL of ethanol was added 0.2 ml con HCl solution. The mixture was stirred at reflux for 2 days. After the solvent was removed under reduced pressure, the residue was purified by reverse-phase preparatory HPLC (26-53% acetonitrile+0.1% trifluoroacetic acid in water+0.1% trifluoroacetic acid, over 15 min.) to give Compound 26 (22 mg, yield 10.4%). 1H NMR (DMSO-d6 400 MHz): δ 8.60 (m, 1H), 7.47-6.36 (m, 11H), 4.87 (m, 1H), 4.03-3.70 (m, 2H), 2.24 (m, 3H), 1.41-1.20 (m, 3H); MS (ESI): m/z 446.0 [M+1]+.

Provenance & Evidence