m-Toluidine → 1-(3-Methylphenyl)-4-oxo-6-methoxy-2,3,4,5-tetrahydropyrrolo[3,2-c]quinoline

HRID 1416675노트

반응식

HRID 1416675 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.[CH3:17][C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][CH:24]=1)[NH2:21]>C1(O)C=CC=CC=1.O>[CH3:17][C:18]1[CH:19]=[C:20]([N:21]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:22]=[CH:23][CH:24]=1

참가 물질

5

반응물 2

HCID 7934m-ToluidineHCID 676260994-Oxo-6-methoxy-2,3-dihydrofuro[3,2-c]quinoline

생성물 1

HCID 570926341-(3-Methylphenyl)-4-oxo-6-methoxy-2,3,4,5-tetrahydropyrrolo[3,2-c]quinoline수율 75.1%

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 in a pressure tube and 3-methylaniline (268 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 sulfate and filtered, and concentrated under reduced pressure. The residue was purified with ethyl acetate as eluent by silica gel chromatography to obtain 230 mg of desired compound as solid in 76% of yield.

후처리

  1. extractionthe aqueous layer was extracted with methylene chloride (15 ml×3)
  2. washAfter washing with water (15 ml×3)
  3. dry with materialthe organic layer was dried by anhydrous magnesium sulfate
  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-70bfec361ec64afaafaeb0f1bbfd0f80
출처 데이터셋
uspto-grants-1999_06
특허 번호
US05914402

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