Hydrochloric Acid → HCID 18385677, compound

Participants

Reaction Conditions

Reaction Steps

To 200 mg of 2,2-dimethyl-4-(4-nitrophenyl)-5-{3-fluoro-4-(methylsulfonyl)-phenyl}-3(2H)-furanone (Example 287) in 7 ml ethanol and 1 ml water, were added 0.5 ml concentrated HCl and 0.2 g of iron powder. The mixture was stirred for 12 hours at 70° C. After the reaction mixture was cooled to room temperature, the unreacted iron was filtered off. The filtrate was concentrated in vacuo and the residue was neutralized with 1 N aqueous sodium hydroxide, which was followed by extraction with 30 ml dichloromethane. The organic layer was concentrated under reduced pressure and was purified by column chromatography (hexane/ethylacetate=1:1) to afford 102 mg of 4-(4-aminophenyl)-2,2-dimethyl-5-{3-fluoro-4-(methylsulfonyl)phenyl}-3(2H)-furanone as a solid. mp: 199-200° C. NMR: δ1.54 (s, 6H), 3.24 (s, 3H), 3.80 (br s, 2H), 6.71 (d, J=8.7 Hz, 2H), 7.06 (d, J=8.7 Hz, 2H), 7.61 (dd, J=10.5, 1.8 Hz, 1H), 7.64 (dd, J=8.4, 1.8 Hz, 1H), 7.92 (dd, J=8.1, 7.2 Hz, 1H). IR (cm−1): 3468, 3374, 1694, 1517, 1386, 1320, 1159, 1147.

Provenance & Evidence