2-Phenylacetophenone → HCID 56644284, compound

Participants

Reaction Steps

A mixture of 1,2-diphenylethanone (150 mg, 0.76 mmol), 3-ethoxy-4-hydroxy-5-nitrobenzaldehyde (194 mg, 0.92 mmol), meldrum's acid (132 mg, 0.92 mmol) and ammonium acetate (71 mg, 0.92 mmol) in acetic acid (5 mL) was refluxed overnight. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (EtOAc: PE=2:1) and prep-HPLC (0.1% TFA as additive) to afford Compound 1 as yellow solid (40 mg, yield: 13%). 1H NMR (DMSO-d6 300 MHz): δ 10.20 (s, 1H), 9.60 (s, 1H), 7.47 (d, J=3.0 Hz, 1H), 7.24-7.18 (m, 6H), 7.01-6.96 (m, 3H), 6.79 (d, J=8.1 Hz, 2H), 4.06 (q, J=6.0 Hz, 2H), 3.96 (d, J=5.1 Hz, 1H), 3.14-3.07 (m, 2H), 1.31 (t, J=7.2 Hz, 3H); MS (ESI): m/z 430.9 [M+H+].

Provenance & Evidence