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

HRID 5133노트

반응식

HRID 5133 반응식
[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

참가 물질

4

반응물 2

HCID 70297m-Chloroperbenzoic acidHCID 57023940HCID 57023940, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
50 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-85ced26261244ccdada566c55d307030
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05243049

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