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Phenylboronic Acid → N-[2-[(6,7-Dimethoxy-4-quinolyl)oxy]-5-methylphenyl]-N-phenylamine

HRID 228522
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 228522
[NH2:1][C:2]1[CH:22]=[C:21]([CH3:23])[CH:20]=[CH:19][C:3]=1[O:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([O:17][CH3:18])=[C:12]([O:15][CH3:16])[CH:13]=2)[N:8]=[CH:7][CH:6]=1.[C:24]1(B(O)O)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(N(CC)CC)C.CN(C)C=O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:16][O:15][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][C:11]=1[O:17][CH3:18])[N:8]=[CH:7][CH:6]=[C:5]2[O:4][C:3]1[CH:19]=[CH:20][C:21]([CH3:23])=[CH:22][C:2]=1[NH:1][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1
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Komponenten

5

Edukt 2

HCID 66827Phenylboronic AcidHCID 230785874-(2-Amino-4-methylphenoxy)-6,7-dimethoxyquinoline

Produkt 1

HCID 23156624N-[2-[(6,7-Dimethoxy-4-quinolyl)oxy]-5-methylphenyl]-N-phenylamineAusbeute 77,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8895Cupric acetateKatalysatorHCID 22056947
triethylamine N,N-dimethylformamide
Lösungsmittel

Versuchsvorschrift

4-(2-Amino-4-methylphenoxy)-6,7-dimethoxyquinoline (52 mg) was dissolved in triethylamine/N,N-dimethylformamide (0.5 ml/2.5 ml), and phenylboronic acid (100 mg) and copper acetate (250 mg) were added to the solution which was then stirred at room temperature overnight. The reaction solution was filtered, and the solvent was removed therefrom by distillation under the reduced pressure. Water was added to the residue, and the mixture was extracted with ethyl acetate. Next, the ethyl acetate layer was then washed with water and saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed therefrom by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using acetone-chloroform to give the title compound (50 mg, yield 76%).

Aufarbeitung

  1. filtrationThe reaction solution was filtered
  2. customthe solvent was removed
  3. distillationby distillation under the reduced pressure
  4. additionWater was added to the residue
  5. extractionthe mixture was extracted with ethyl acetate
  6. washNext, the ethyl acetate layer was then washed with water and saturated brine
  7. dry with materialwas dried over anhydrous sodium sulfate
  8. customThe solvent was removed
  9. distillationby distillation under the reduced pressure
  10. customthe residue was purified by thin layer chromatography

Quellen und Nachweise

ORD-Eintrag
ord-cb2c590698844012b3e2a9628d8f6546
Quelldatensatz
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07560558B2

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