Ethyl 4-amino-3-(3-chlorophenyl)butanoate → 4-(3-Chlorophenyl)pyrrolidin-2-one

HRID 453245Notes

Reaction equation

HRID 453245 reaction equation
[NH2:1][CH2:2][CH:3]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=1)[CH2:4][C:5](OCC)=[O:6]>C1(C)C=CC=CC=1>[Cl:16][C:12]1[CH:11]=[C:10]([CH:3]2[CH2:2][NH:1][C:5](=[O:6])[CH2:4]2)[CH:15]=[CH:14][CH:13]=1

Participants

3

Reactant 1

HCID 22387061Ethyl 4-amino-3-(3-chlorophenyl)butanoate

Product 1

HCID 179489414-(3-Chlorophenyl)pyrrolidin-2-oneYield 49.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a 500 ml flask fitted with reflux condenser and magnetic stirrer, 135.7 g (561 mmoles) of ethyl 4-amino-3-(3-chlorophenyl)butanoate 378 are dissolved in 200 ml of toluene, and the mixture is refluxed for 30 min. The solution is concentrated to dryness and the residue purified by PrepLC (1 kg SiO2, CH2Cl2/EtOH, 98:2→95:5) to give 54.4 g of pure 379 (49.2%). GC/MS: 197/197 M+.

Workup

  1. customIn a 500 ml flask fitted
  2. temperaturewith reflux condenser and magnetic stirrer
  3. temperaturethe mixture is refluxed for 30 min
  4. concentrationThe solution is concentrated to dryness
  5. customthe residue purified by PrepLC (1 kg SiO2, CH2Cl2/EtOH, 98:2→95:5)

Sources & evidence

ORD record
ord-1bd4a17b07c144a794dba2c2db616963
Source dataset
uspto-grants-2013_07
Patent number
US08492416B2

Reaction notes

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