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

HRID 1805131

Reaktionsgleichung

Reaktionsgleichung von HRID 1805131
[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]

Komponenten

4

Edukt 2

HCID 7922Succinic anhydrideHCID 805742-tert-Butylaniline

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

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)).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-27602b7047e14a4e891deee1edf295c3
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08354427B2

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