Hydrochloric Acid → 4-(4-Chlorophenyl)-2-pyrrolidinone

HRID 1402840

Reaktionsgleichung

Reaktionsgleichung von HRID 1402840
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:15][N+:16]([O-])=O)[CH2:9][C:10](OCC)=[O:11])=[CH:4][CH:3]=1.Cl>C(O)(=O)C.[Fe]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:15][NH:16][C:10](=[O:11])[CH2:9]2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 11097654HCID 11097654, Verbindung

Produkt 1

HCID 1854904-(4-Chlorophenyl)-2-pyrrolidinoneAusbeute 51,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

The solution of ethyl 3-(4-chlorophenyl)-4-nitrobutanoate (2.33 g) in acetic acid (18 ml) was stirred vigorously while iron powder (5.7 g) was added. The suspension was stirred at reflux temperature for 1.5 h. The resulting thick slurry was pored into a mixture of conc. HCl (30 ml) and ice (30 g). The aqueous layer was extracted with dichloromethane (2×50 ml) and the combined organic layers washed with water and dried (sodium sulfate). After evaporation of the solvent the oily residue was distilled with toluene to remove acetic acid whereupon crystallisation took place. The crude was washed with diethyl ether (3×2 ml) and dried in vacuo to afford 4-(4-chlorophenyl)-2-pyrrolidone (0.86 g) as colourless crystals.

Aufarbeitung

  1. additionwas added
  2. temperatureat reflux temperature for 1.5 h
  3. extractionThe aqueous layer was extracted with dichloromethane (2×50 ml)
  4. washthe combined organic layers washed with water
  5. dry with materialdried (sodium sulfate)
  6. customAfter evaporation of the solvent the oily residue
  7. distillationwas distilled with toluene
  8. customto remove acetic acid
  9. customwhereupon crystallisation
  10. washThe crude was washed with diethyl ether (3×2 ml)
  11. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-68de09f4b17c4e0b93befe269f3f079f
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08912186B2

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