Hydrochloric Acid → HCID 51348217, compound

Participants

Reaction Steps

To a solution of 3-(2-phenylacetyl)benzonitrile (Intermediate 23) (100 mg, 0.45 mmol), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (89.1 mg, 0.45 mmol), and urea (82.3 mg, 1.35 mmol) in 5 mL of ethanol was added 0.2 mL of concentrated HCl, 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 53 (18.2 mg, yield 8.8%). 1H NMR (DMSO-d6 400 MHz) δ 10.27 (s, 1H), 8.86 (s, 1H), 7.71 (t, J=12.4 Hz, 2H), 7.57 (s, 1H), 7.44 (m, 3H), 7.14-7.06 (m, 4H), 6.85 (d, J=6.8 Hz, 2H), 5.28 (s, 1H), 4.06 (m, 2H), 1.32 (t, J=6.8 Hz, 3H); MS (ESI): m/z 456.9 [M+1]+.

Provenance & Evidence