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Water → 6-[(6,7-Dimethoxy-4-quinolyl)oxy]-1,4-dihydro-2H-3,1-benzoxazin-2-one

HRID 228535
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 228535
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([O:19][CH3:20])[CH:17]=3)[N:12]=[CH:11][CH:10]=2)=[CH:4][C:3]=1[CH2:23][OH:24].Cl[C:26](Cl)([O:28]C(=O)OC(Cl)(Cl)Cl)Cl.O>C(N(CC)CC)C.C1(C)C=CC=CC=1>[CH3:20][O:19][C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][C:15]=1[O:21][CH3:22])[N:12]=[CH:11][CH:10]=[C:9]2[O:8][C:5]1[CH:6]=[CH:7][C:2]2[NH:1][C:26](=[O:28])[O:24][CH2:23][C:3]=2[CH:4]=1
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Komponenten

5

Edukt 3

HCID 962WaterHCID 94429TriphosgeneHCID 68830546{2-Amino-5-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}methanol

Produkt 1

HCID 231564336-[(6,7-Dimethoxy-4-quinolyl)oxy]-1,4-dihydro-2H-3,1-benzoxazin-2-oneAusbeute 39 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 22504574Toluene triethylamineLösungsmittel

Versuchsvorschrift

{2-Amino-5-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}methanol (63 mg) was dissolved in heated triethylamine/toluene (1.2 ml/6 ml) to prepare a solution. Triphosgene (98 mg) was added to the solution and was heated under reflux for 2 min. The reaction solution was cooled to room temperature, water was then added to the reaction solution, and the mixture was extracted with chloroform. The chloroform 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 column chromatography on silica gel using acetone-chloroform to give the title compound (24 mg, yield 39%).

Aufarbeitung

  1. customto prepare a solution
  2. temperaturewas heated
  3. temperatureunder reflux for 2 min
  4. extractionthe mixture was extracted with chloroform
  5. washThe chloroform layer was then washed with water and saturated brine
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. customThe solvent was removed
  8. distillationby distillation under the reduced pressure
  9. customthe residue was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-f33e7705410f4bfdb218846039397b48
Quelldatensatz
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07560558B2

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