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Sodium Iodide → 2-Fluoro-4-[(6-methoxy-7-(3-morpholinopropyl)-4-quinolyl)oxy]aniline

HRID 31152
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HRID 31152 반응식
[F:1][C:2]1[CH:8]=[C:7]([O:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([CH2:22][CH2:23][CH2:24]Cl)=[C:17]([O:20][CH3:21])[CH:18]=3)[N:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][C:3]=1[NH2:4].[C:26](=[O:29])([O-])[O-].[K+].[K+].[I-].[Na+].FC1C=CC([CH2:41][C:42](O)=O)=CC=1.[CH3:45][N:46](C)C=O>C(Cl)(Cl)Cl.CO>[F:1][C:2]1[CH:8]=[C:7]([O:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([CH2:22][CH2:23][CH2:24][N:46]4[CH2:45][CH2:26][O:29][CH2:42][CH2:41]4)=[C:17]([O:20][CH3:21])[CH:18]=3)[N:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][C:3]=1[NH2:4]
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참가 물질

7

반응물 5

HCID 5238Sodium IodideHCID 6228DimethylformamideHCID 98372-(4-Fluorophenyl)acetic acidHCID 11430Potassium CarbonateHCID 671970732-Fluoro-4-[(7-(3-chloropropyl)-6-methoxy-4-quinolyl)oxy]aniline

생성물 1

HCID 671966402-Fluoro-4-[(6-methoxy-7-(3-morpholinopropyl)-4-quinolyl)oxy]aniline
수율 76%

시약·촉매·용매 1

HCID 21584188Chloroform methanol용매

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온도
70 °C

실험 절차

The aniline compound (0.7 g) prepared in step 1) was dissolved in dimethylformamide (40 ml) to prepare a solution. Potassium carbonate (1.4 g), sodium iodide (0.6 g) and moripholine (0.85 g) (starting compound B) were added to the solution, and the mixture was stirred at 70° C. for 20 hr. The reaction solution was extracted with ethyl acetate, followed by washing with saturated brine. The extract was dried over anhydrous sodium sulfate, and the solvent was removed by evaporation under the reduced pressure. The residue was purified by column chromatography on silica gel, and the title compound (0.64 g, yield 76%) was obtained from the fraction of chloroform:methanol (95:5).

후처리

  1. customto prepare a solution
  2. extractionThe reaction solution was extracted with ethyl acetate
  3. washby washing with saturated brine
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. customthe solvent was removed by evaporation under the reduced pressure
  6. customThe residue was purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-84cc826f0b834b4a8d693567a5418566
출처 데이터셋
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07425564B2

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