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Hydrochloric Acid → 4-Ethyl-3-(3-chlorophenyl)-1-(3-isopropylphenyl)pyrrolidine-2-one

HRID 486299
Notes
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Reaction equation

HRID 486299 reaction equation
[CH2:1]([C:3]1[CH2:7][N:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH:14]([CH3:16])[CH3:15])[CH:9]=2)[C:5](=[O:17])[C:4]=1[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=1)[CH3:2].B.[Na].CO.Cl>O1CCCC1>[CH2:1]([CH:3]1[CH2:7][N:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH:14]([CH3:16])[CH3:15])[CH:9]=2)[C:5](=[O:17])[CH:4]1[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=1)[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 117275204-Ethyl-3-(3-chlorophenyl)-1-(3-isopropylphenyl)-3-pyrroline-2-oneHCID 178418435HCID 178418435, compound

Product 1

HCID 190978064-Ethyl-3-(3-chlorophenyl)-1-(3-isopropylphenyl)pyrrolidine-2-oneYield 89.5%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

5.0 g (14.7 mmol) of 4-ethyl-3-(3-chlorophenyl)-1-(3-isopropylphenyl)-3-pyrroline-2-one synthesized in Example 4 and 0.56 g (14.7 mmol) of sodium boron hydride were dissolved in 70 ml of tetrahydrofuran, and 11 ml of methanol were slowly added to the solution over about 1 hour, while the solution was heated under reflux. Reaction was allowed to proceed at the same temperature for further 1 hour, and the reaction mixture was then poured into 1 N hydrochloric acid, followed by extraction with ethyl acetate. The resultant organic layer was washed with water, an aqueous saturated sodium bicarbonate solution and water in this order, and then dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and n-hexane was then added to the resultant residue to achieve crystallization, followed by recrystallization from etherpetroleum ether, thereby obtaining 4.5 g of the desired product in the state of colorless crystals (yield 90%). m.p. 88.5°-90.0° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. customReaction
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe resultant organic layer was washed with water
  6. dry with materialan aqueous saturated sodium bicarbonate solution and water in this order, and then dried over magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure, and n-hexane
  8. additionwas then added to the resultant residue
  9. customcrystallization
  10. customfollowed by recrystallization from etherpetroleum ether

Sources & evidence

ORD record
ord-bfafabb2be224685bf37f010c8a60413
Source dataset
uspto-grants-1994_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05290949

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes