Hydrochloric Acid → HCID 18385677, compound

HRID 2298325Notes

Reaction equation

HRID 2298325 reaction equation
[CH3:1][C:2]1([CH3:28])[C:6](=[O:7])[C:5]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=2)=[C:4]([C:17]2[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[C:19]([F:27])[CH:18]=2)[O:3]1.Cl>C(O)C.O.[Fe]>[NH2:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]2[C:6](=[O:7])[C:2]([CH3:1])([CH3:28])[O:3][C:4]=2[C:17]2[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:24])=[O:25])=[C:19]([F:27])[CH:18]=2)=[CH:9][CH:10]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 18385805HCID 18385805, compound

Product 1

HCID 18385677HCID 18385677, compoundYield 55.1%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

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.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. filtrationthe unreacted iron was filtered off
  3. concentrationThe filtrate was concentrated in vacuo
  4. extractionwas followed by extraction with 30 ml dichloromethane
  5. concentrationThe organic layer was concentrated under reduced pressure
  6. customwas purified by column chromatography (hexane/ethylacetate=1:1)

Sources & evidence

ORD record
ord-6b758428e0004e45883dfd54a9dd4073
Source dataset
uspto-grants-2002_12
Patent number
US06492416B1

Reaction notes

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