2-Methyl-4-methoxyaniline → 1-(2-Methyl-4-methoxyphenyl)-4-oxo-6-methoxy-2,3,4,5-tetrahydropyrrolo[3,2-c]quinoline

HRID 1416673노트

반응식

HRID 1416673 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][O:18][C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[C:21]([CH3:26])[CH:20]=1>C(O)CO.O>[CH3:26][C:21]1[CH:20]=[C:19]([O:18][CH3:17])[CH:25]=[CH:24][C:22]=1[N:23]1[C:10]2[C:9]3[CH:8]=[CH:7][CH:6]=[C:5]([O:15][CH3:16])[C:4]=3[NH:3][C:2](=[O:1])[C:11]=2[CH2:12][CH2:13]1

참가 물질

5

반응물 2

HCID 76102-Methyl-4-methoxyanilineHCID 676260994-Oxo-6-methoxy-2,3-dihydrofuro[3,2-c]quinoline

생성물 1

HCID 110676751-(2-Methyl-4-methoxyphenyl)-4-oxo-6-methoxy-2,3,4,5-tetrahydropyrrolo[3,2-c]quinoline수율 80.3%

시약·촉매·용매 2

HCID 174Ethylene Glycol용매HCID 962Water용매

반응 조건

온도
210 °C

실험 절차

4-Oxo-6-methoxy-2,3-dihydrofuro[3,2-c]quinoline (217 mg, 1.0 mmol) was dissolved in 10 ml of ethylene glycol and 4-methoxy-2-methylaniline (322 μl, 2.5 mmol) was added under nitrogen. The reaction mixture was heated at 210° 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 270 mg of desired compound as solid in 81% 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-72f74d6522de4594a94da94717e0f0d9
출처 데이터셋
uspto-grants-1999_06
특허 번호
US05914402

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