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Hydrochloric Acid → HCID 21889971, Verbindung

HRID 721603
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 721603
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=O)[CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20]3[C:29]4[C:24](=[CH:25][C:26]([O:32][CH3:33])=[C:27]([O:30][CH3:31])[CH:28]=4)[N:23]=[CH:22][CH:21]=3)=[CH:15][CH:14]=2)=[CH:5][CH:4]=1.Cl.[OH-].[Na+]>O1CCCC1>[CH3:31][O:30][C:27]1[CH:28]=[C:29]2[C:24](=[CH:25][C:26]=1[O:32][CH3:33])[N:23]=[CH:22][CH:21]=[C:20]2[O:19][C:16]1[CH:15]=[CH:14][C:13]([O:12][CH2:11][CH2:10][NH:9][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)=[CH:18][CH:17]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21891203HCID 21891203, Verbindung

Produkt 1

HCID 21889971HCID 21889971, VerbindungAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

N1-(4-Methoxyphenyl)-2-{4-[(6,7-dimethoxy-4-quinolyl)oxy]phenoxy}acetamide (90 mg) was dissolved in tetrahydrofuran (10 ml) to prepare a solution. A borane-tetrahydrofuran complex (1.0 M solution: 0.98 ml) was then added to the solution, and the mixture was heated under reflux for 3 hr. 1 N Hydrochloric acid was added thereto, and the mixture was further heated under reflux for 30 min. A 5% aqueous sodium hydroxide solution was added to the reaction solution, the mixture was extracted with chloroform, and the extract was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was purified by thin-layer chromatography using chloroform/methanol for development to give the title compound (52 mg, yield 60%).

Aufarbeitung

  1. customto prepare a solution
  2. additionA borane-tetrahydrofuran complex (1.0 M solution: 0.98 ml) was then added to the solution
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 3 hr
  5. temperaturethe mixture was further heated
  6. temperatureunder reflux for 30 min
  7. extractionthe mixture was extracted with chloroform
  8. dry with materialthe extract was dried over anhydrous sodium sulfate
  9. customThe solvent was removed by distillation under the reduced pressure
  10. customThe residue was purified by thin-layer chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b225fac4d8dc4fea85d13426d18ac1b7
Quelldatensatz
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07135466B2

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