Hydrochloric Acid → HCID 66826097, compound

Participants

Reaction Steps

To a solution of 1-(4-(dimethylamino)phenyl)-2-phenylethanone (80 mg, 0.32 mmol), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (63 mg, 0.32 mmol), and urea (60 mg, 0.96 mmol) in 5 mL of ethanol was added 0.2 mL of concentrated HCl solution, and the mixture was refluxed 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 54 (27 mg, yield 16.3%). 1H NMR (DMSO-d6 400 MHz TMS): δ 10.29 (s, 1H), 8.51 (s, 1H), 7.47 (d, J=8.8 Hz, 2H), 7.23 (s, 1H), 7.07-6.97 (m, 5H), 6.83 (d, J=7.2 Hz, 2H), 6.58 (d, J=8.4 Hz, 2H), 5.07 (d, J=2.4 Hz, 1H), 4.05 (q, J=6.8 Hz, 2H), 2.88 (s, 6H), 1.34 (t, J=6.8 Hz, 3H); MS (ESI): m/z 475.0 [M+1]+.

Provenance & Evidence