m-Chloroperbenzoic acid → 2-Phenyl-pyrrolo[3,4-c]quinoline-3(1H),4(5H)-dione

HRID 1415717ノート

反応式

HRID 1415717 の反応式
[C:1]1([N:7]2[CH2:19][C:18]3[C:17]4[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=4[N:11]=[CH:10][C:9]=3[C:8]2=[O:20])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1C=CC=C(C(OO)=[O:29])C=1>C(Cl)Cl>[C:1]1([N:7]2[CH2:19][C:18]3[C:17]4[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=4[NH:11][C:10](=[O:29])[C:9]=3[C:8]2=[O:20])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

4

反応物 2

HCID 70297m-Chloroperbenzoic acidHCID 57023940HCID 57023940、化合物

生成物 1

HCID 138117802-Phenyl-pyrrolo[3,4-c]quinoline-3(1H),4(5H)-dione

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
50 °C

実験手順

A mixture of 2-Phenyl-pyrrolo[3,4-c]quinolin-3(1H)-one (60 mg), and m-chloroperbenzoic acid (105 mg) in 3 mL of methylene chloride was kept at room temperature for 24 h. The mixture was diluted with methylene chloride and washed with sodium carbonate solution. The organic layer was dried over magnesium sulfate and the solvent was removed in vacuo. The residue was heated at 50° C. for 3 h with 1 mL of acetic anhydride. The reaction was quenched with methanol and made basic with ammonium hydroxide. The reaction mixture was concentrated in vacuo, and the resulting aqueous solution was extracted with ethyl acetate, the organic layer was dried over magnesium sulfate and the solvent was removed in vacuo. The residue was triturated with ether to afford 2-Phenyl-pyrrolo[3,4-c]quinoline-3(1H),4(5H)-dione (Compound 16) as a white solid.

後処理

  1. washwashed with sodium carbonate solution
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. customthe solvent was removed in vacuo
  4. customThe reaction was quenched with methanol
  5. concentrationThe reaction mixture was concentrated in vacuo
  6. extractionthe resulting aqueous solution was extracted with ethyl acetate
  7. dry with materialthe organic layer was dried over magnesium sulfate
  8. customthe solvent was removed in vacuo
  9. customThe residue was triturated with ether

出典と根拠

ORDレコード
ord-589e496fb2124902a29c539e315a3cda
出典データセット
uspto-grants-1999_06
特許番号
US05908932

反応ノート

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