Succinic anhydride → 4-[(2-Tert-butylphenyl)amino]-4-oxobutanoic acid

HRID 1915472

Reaction equation

HRID 1915472 reaction equation
[C:1]([C:5]1[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=1[NH2:7])([CH3:4])([CH3:3])[CH3:2].[O:12]1[C:16](=[O:17])[CH2:15][CH2:14][C:13]1=[O:18]>C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=1[NH:7][C:16](=[O:17])[CH2:15][CH2:14][C:13]([OH:18])=[O:12])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 7922Succinic anhydrideHCID 805742-tert-Butylaniline

Product 1

HCID 64683564-[(2-Tert-butylphenyl)amino]-4-oxobutanoic acid

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2-tert-butylaniline (1.0 g, 6.7 mmol) in toluene (15 mL) was added tetrahydrofuran-2,5-dione (0.81 g, 8.1 mmol) and the reaction mixture was refluxed for 1 h. The reaction mixture was cooled and filtered to obtain 4-(2-tert-butylphenylamino)-4-oxobutanoic acid, which was dissolved in acetic acid (20 mL) and sodium acetate (3.02 g, 36.86 mmol) and was stirred at 80° C. overnight. The reaction was quenched with water, the layers separated and the aqueous layer was extracted with DCM. The combined organic layer was dried over MgSO4, filtered and concentrated. The resulting solid was recrystallized from ethanol, to obtain pure 1-(2-tert-butylphenyl)pyrrolidine-2,5-dione (930 mg, 60%). LC/MS: m/z 232.3 (M+H)+ at 1.264 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. temperaturethe reaction mixture was refluxed for 1 h
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered

Sources & evidence

ORD record
ord-b3aa687bee1c442e9c91b5c12829717e
Source dataset
uspto-grants-2013_12
Patent number
US08614327B2

Linked notes

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