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

HRID 1915472

반응식

HRID 1915472 반응식
[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]

참가 물질

4

반응물 2

HCID 7922Succinic anhydrideHCID 805742-tert-Butylaniline

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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)).

후처리

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

출처 및 근거

ORD 기록
ord-b3aa687bee1c442e9c91b5c12829717e
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08614327B2

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