Hydrochloric Acid → HCID 51349218, compound

Participants

Reaction Steps

To the solution of 4-hydroxy-3-(2-hydroxyethoxy)-5-nitrobenzaldehyde (Intermediate 71) (60 mg, 0.27 mmol), 1,2-diphenyl-ethanone (53 mg, 0.27 mmol) and urea (48.6 mg, 0.81 mmol) in 4 mL of ethanol was added 0.2 mL of concentrated HCl, and the mixture was stirred at reflux for 2 days. The mixture was concentrated and 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 137 (28 mg, yield 23.7%). 1H NMR (DMSO-d6 400 MHz): δ 10.23 (s, 1H), 8.75 (s, 1H), 7.55 (s, 1H), 7.46 (s, 1H), 7.26 (m, 6H), 7.02 (m, 3H), 6.83 (d, J=7.2 Hz, 2H), 5.19 (d, J=2.4 Hz, 1H), 3.99 (m, 2H), 3.75 (m, 2H); MS (ESI): m/z 448.1 [M+1]+.

Provenance & Evidence