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

HRID 1915472

反応式

HRID 1915472 の反応式
[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]

参加物

4

反応物 2

HCID 7922Succinic anhydrideHCID 805742-tert-Butylaniline

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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)).

後処理

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

出典と根拠

ORDレコード
ord-b3aa687bee1c442e9c91b5c12829717e
出典データセット
uspto-grants-2013_12
特許番号
US08614327B2

関連ノート

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