Aniline → 1-(Phenyl)-4-oxo-6-methoxy-2,3,4,5-tetrahydropyrrolo[3,2-c]quinoline

HRID 1416670노트

반응식

HRID 1416670 반응식
[O:1]=[C:2]1[CH:11]2[CH2:12][CH2:13]O[C:10]2=[C:9]2[C:4]([C:5]([O:15][CH3:16])=[CH:6][CH:7]=[CH:8]2)=[N:3]1.[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1(O)C=CC=CC=1.O>[C:18]1([N:17]2[C:10]3[C:9]4[CH:8]=[CH:7][CH:6]=[C:5]([O:15][CH3:16])[C:4]=4[NH:3][C:2](=[O:1])[C:11]=3[CH2:12][CH2:13]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

참가 물질

5

반응물 2

HCID 6115AnilineHCID 676260994-Oxo-6-methoxy-2,3-dihydrofuro[3,2-c]quinoline

생성물 1

HCID 158088531-(Phenyl)-4-oxo-6-methoxy-2,3,4,5-tetrahydropyrrolo[3,2-c]quinoline수율 82.1%

시약·촉매·용매 2

HCID 962Water용매HCID 996Phenol용매

반응 조건

온도
190 °C

실험 절차

4-Oxo-6-methoxy-2,3-dihydrofuro[3,2-c]quinoline (217 mg, 1.0 mmol) was dissolved in 7 ml of phenol and aniline (228 μl, 2.5 mmol) was added under nitrogen. The reaction mixture was heated at 190° C. for 15 hours. The reaction mixture was diluted with 20 ml of salt water and the aqueous layer was extracted with methylene chloride (15 ml×3). After washing with water (15 ml×3), the organic layer was dried by anhydrous magnesium surface and filtered, and concentrated under reduced pressure. The residue was purified with ethyl acetate as eluent by silica gel chromatography to obtain 240 mg of desired compound as solid in 83% of yield.

후처리

  1. extractionthe aqueous layer was extracted with methylene chloride (15 ml×3)
  2. washAfter washing with water (15 ml×3)
  3. customthe organic layer was dried by anhydrous magnesium surface
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified with ethyl acetate as eluent by silica gel chromatography

출처 및 근거

ORD 기록
ord-36e47219e5a74fd0ba239f883256b0d5
출처 데이터셋
uspto-grants-1999_06
특허 번호
US05914402

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