Hydrochloric Acid → HCID 51348807, compound

Participants

Reaction Steps

A mixture of 1-(naphthalen-2-yl)-2-phenylethanone (Intermediate 43) (260 mg, 1.06 mmol), -ethoxy-4-hydroxy-5-nitrobenzaldehyde (267.6 mg, 1.27 mmol), and urea (190.2 mg, 3.17 mmol) in anhydrous EtOH (5 mL) was added concentrated HCl solution (0.2 mL), and the reaction mixture was refluxed for 14 hours. The reaction mixture was concentrated under reduce pressure, and the residue was purified by column chromatography (EtOAc:MeOH=50:1) and preparative HPLC to afford Compound 85 as a yellow solid (64 mg, yield: 12.6%). 1H NMR (DMSO-d6 400 MHz): δ 10.12 (d, J=12.0 Hz, 1H), 8.65 (d, J=16.0 Hz, 1H), 7.67-7.81 (m, 3H), 7.30-7.46 (m, 5H), 6.99-7.18 (m, 2H), 6.58-6.73 (m, 5H), 5.14-5.35 (m, 1H), 3.90-3.96 (m, 2H), 1.16-1.22 (m, 3H); MS (ESI): m/z 482.1 [M+1]+.

Provenance & Evidence