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

HRID 1402840Notes

Reaction equation

HRID 1402840 reaction equation
[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

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 11097654Ethyl 3-(4-chlorophenyl)-4-nitrobutanoate

Product 1

HCID 1854904-(4-Chlorophenyl)-2-pyrrolidinoneYield 51.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-68de09f4b17c4e0b93befe269f3f079f
Source dataset
uspto-grants-2014_12
Patent number
US08912186B2

Reaction notes

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