Methanesulfonic Acid → HCID 21939646, compound

Participants

Reaction Conditions

Reaction Steps

A solution of N-[2-(4-hydroxybenzyl)phenyl]acetamide (200 mg, 0.83 mmol) in CF3COCH2CO2Et (305 mg, 1.66 mmol) & MeSO3H (750 μL, 11.55 mmol) was heated at 75° C. for 2 d. On cooling to 20° C., the mixture was treated with H2O (20 mL), then the pH was adjusted to 12 with NaOH. The mixture was extracted with EtOAc (150 mL), then the extracts were washed with 0.5 M NaOH (2×50 mL), before being dried (MgSO4). Filtration, solvent evaporation, & column chromatography (1:2 PE-EtOAc) yielded N-[2-(2-oxo-4-trifluoromethyl-2H-chromen-6-ylmethyl)-phenyl]acetamide (78 mg, 26%): m/z (ES+)=362.2 [M+H]+. A solution of this compound in AcOH-12 M HCl (1:6, 3.5 mL) was heated at 95° C. for 6 h. On cooling to 20° C., H2O (8 mL) was added, then the mixture was treated with NaOH then Na2CO3 to adjust the pH to 10. Extraction with EtOAc (10 mL) & solvent evaporation furnished a residue which was subjected to column chromatography (2:1 PE-EtOAc) to give the title compound (8 mg, 12%): δH (CDCl3)=3.50 (br s, 2H), 4.00 (s, 2H), 6.70 (d, 1H), 6.80 (m, 2H), 7.00 (d, 1H), 7.10 (t, 1H), 7.35 (d, 1H), 7.40 (d, 1H), 7.55 (s, 1H); m/z (ES+)=320.1 [M+H]+. Compounds of Formula I

Provenance & Evidence