3-(Trifluoromethyl)aniline → 3-Carboxy-1-(3-trifluoromethylphenyl)-2-pyrrolidinone

HRID 889031Notes

Reaction equation

HRID 889031 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([NH2:9])[CH:6]=[CH:7][CH:8]=1.CC1(C)[O:20][C:19](=O)[C:16]2([CH2:18][CH2:17]2)[C:15](=[O:22])[O:14]1>ClCCl>[O:20]=[C:19]1[CH:16]([C:15]([OH:22])=[O:14])[CH2:17][CH2:18][N:9]1[C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:10])([F:11])[F:1])[CH:4]=1

Participants

4

Reactant 2

HCID 73753-(Trifluoromethyl)anilineHCID 797206,6-Dimethyl-5,7-dioxaspiro(2.5)octane-4,8-dione

Product 1

HCID 155160613-Carboxy-1-(3-trifluoromethylphenyl)-2-pyrrolidinoneYield 69.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
22.5 °C

Procedure

A mixture of 3-trifluoromethyl-phenylamine (2.8 g, 17.5 mmol) and 6,6-dimethyl-5,7-dioxa-spiro[2.5]octane-4,8-dione (1.0 g, 5.8 mmol) was stirred at 20-25° C. for 18 hrs. The reaction mixture was diluted with dichloromethane and washed with 10% NaOH solution (3×10 ml). The aqueous layer was cooled and acidified with dil HCl. The aqueous layer was extracted with dichloromethane, washed with saturated brine solution. The organic layer was dried over Na2SO4 and evaporated to obtain 2-oxo-1-(3-trifluoromethyl-phenyl)-pyrrolidine-3-carboxylic acid (1.1 g, 69%) as an off white solid.

Workup

  1. washwashed with 10% NaOH solution (3×10 ml)
  2. temperatureThe aqueous layer was cooled
  3. extractionThe aqueous layer was extracted with dichloromethane
  4. washwashed with saturated brine solution
  5. dry with materialThe organic layer was dried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-0a96394d33484adab5373ccf931222b3
Source dataset
uspto-grants-2012_08
Patent number
US08252797B2

Reaction notes

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