Hydrochloric Acid → Ethyl 1-(4-chlorophenyl)-2-oxopyrrolidine-3-carboxylate

HRID 1740377Notes

Reaction equation

HRID 1740377 reaction equation
[H-].[Na+].[C:3](=[O:10])([O:7][CH2:8][CH3:9])OCC.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:22][CH2:21][CH2:20][C:19]2=[O:23])=[CH:14][CH:13]=1.Cl>O1CCCC1.CCCCCC>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:22][CH2:21][CH:20]([C:3]([O:7][CH2:8][CH3:9])=[O:10])[C:19]2=[O:23])=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7766Diethyl CarbonateHCID 24758Sodium hydrideHCID 27247131-(4-Chlorophenyl)-2-pyrrolidinone

Product 1

HCID 18544410Ethyl 1-(4-chlorophenyl)-2-oxopyrrolidine-3-carboxylateYield 84.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

To a suspension of 25 g of sodium hydride (60% oil dispersion) in 100 mL of tetrahydrofuran was added 37 g of diethyl carbonate. Under reflux, to the mixture was added dropwise a solution of 52.0 g of 1-(4-chlorophenyl)-2-pyrrolidinone in 150 mL of tetrahydrofuran over about 1.5 hours. After refluxing for 4.5 hours, the reaction mixture was cooled, and carefully poured into ice-water. The mixture was made to weakly alkaline with diluted hydrochloric acid and extracted with 300 mL of ethyl acetate. The organic layer was washed sequentially with water, aqueous sodium bicarbonate solution and water, dried over anhydrous magnesium sulfate and concentrated to give an oil. To the residue was added 200 mL of n-hexane, and the precipitated crystals were collected by filtration. The crystals were washed with n-hexane and dried in vacuo to give 60 g of the title compound.

Workup

  1. temperatureUnder reflux, to the mixture
  2. temperatureAfter refluxing for 4.5 hours
  3. temperaturethe reaction mixture was cooled
  4. extractionextracted with 300 mL of ethyl acetate
  5. washThe organic layer was washed sequentially with water, aqueous sodium bicarbonate solution and water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customto give an oil
  9. filtrationthe precipitated crystals were collected by filtration
  10. washThe crystals were washed with n-hexane
  11. customdried in vacuo

Sources & evidence

ORD record
ord-b6f6a745cc304180b3fed81978ca0555
Source dataset
uspto-grants-1999_10
Patent number
US05969138

Reaction notes

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