Ethyl 4-amino-4-(3-methoxyphenyl)butanoate → 5-(3-Methoxyphenyl)-2-pyrrolidinone

HRID 233013Notes

Reaction equation

HRID 233013 reaction equation
[NH2:1][CH:2]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=1)[CH2:3][CH2:4][C:5](OCC)=[O:6]>C1(C)C=CC=CC=1>[CH3:17][O:16][C:12]1[CH:11]=[C:10]([CH:2]2[NH:1][C:5](=[O:6])[CH2:4][CH2:3]2)[CH:15]=[CH:14][CH:13]=1

Participants

3

Reactant 1

HCID 23361303Ethyl 4-amino-4-(3-methoxyphenyl)butanoate

Product 1

HCID 152932255-(3-Methoxyphenyl)-2-pyrrolidinoneYield 90%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Ethyl 4-amino-4-(3-methoxyphenyl)butanoate (9.39 g) was dissolved in toluene (50 ml) and the solution heated under reflux for 0.5 hr to 1.0 hr. The mixture was cooled to ambient temperature, the precipitate was collected, and the filtrate was concentrated. The residue was recrystallized from ether to give 6.80 g (90%) of product, mp 84°-85° C.

Workup

  1. temperaturethe solution heated
  2. temperatureunder reflux for 0.5 hr to 1.0 hr
  3. customthe precipitate was collected
  4. concentrationthe filtrate was concentrated
  5. customThe residue was recrystallized from ether

Sources & evidence

ORD record
ord-925a4b518fad48d7b89d204dd678c834
Source dataset
uspto-grants-1997_01
Patent number
US05591856

Reaction notes

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