4-Fluoro-2-methylaniline → 1-(2-Methyl-4-fluorphenyl)-4-oxo-6-methoxy-2,3,4,5-tetrahydropyrrolo[3,2-c]quinoline

HRID 1416674노트

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HRID 1416674 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.[F:17][C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[C:20]([CH3:25])[CH:19]=1>C(O)COCCO.O>[CH3:25][C:20]1[CH:19]=[C:18]([F:17])[CH:24]=[CH:23][C:21]=1[N:22]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 679824-Fluoro-2-methylanilineHCID 676260994-Oxo-6-methoxy-2,3-dihydrofuro[3,2-c]quinoline

생성물 1

HCID 675987851-(2-Methyl-4-fluorphenyl)-4-oxo-6-methoxy-2,3,4,5-tetrahydropyrrolo[3,2-c]quinoline수율 78.9%

시약·촉매·용매 2

HCID 962Water용매HCID 8117Diethylene Glycol용매

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온도
250 °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 diethylene glycol in a pressure tube and (278 μl, 2.5 mmol) of 4-fluor-2-methylaniline (278 μl, 2.5 mmol) was added under nitrogen. The reaction mixture was heated at 250° 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 according to silica gel chromatography to obtain 256 mg of desired compound as solid in 79% 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

출처 및 근거

ORD 기록
ord-da83956fef614cada01d53579570b2ab
출처 데이터셋
uspto-grants-1999_06
특허 번호
US05914402

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