Ethylene carbonate → 2-(2-Amino-8-quinolinyloxy)-ethanol

HRID 1789741Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1789741
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([OH:12])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.C1(=O)O[CH2:16][CH2:15][O:14]1.O(C(C)(C)C)[K]>CN(C=O)C.[Cl-].[Na+].O>[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([O:12][CH2:16][CH2:15][OH:14])[CH:6]=[CH:7][CH:8]=2)[N:3]=1

Komponenten

6

Edukt 3

HCID 7303Ethylene carbonateHCID 46537882-Amino-8-quinolinolHCID 178418922HCID 178418922, Verbindung

Produkt 1

HCID 220362542-(2-Amino-8-quinolinyloxy)-ethanolAusbeute 28 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 2-amino-8-quinolinol (3.20 g, 20.0 mmol), ethylene carbonate (1.76 g, 20.0 mmol) and KO-t-Bu (2.24 g, 20.0 mmol) in DMF (20 mL) was stirred at 90° C. for 15 h. The mixture was poured into brine, extracted with EtOAc, dried (MgSO4), and concentrated under reduced pressure. The residue was purified by chromatography on silica gel using toluene/EtOAc/MeOH (50:50:2) as eluent to give 1.13 g (28%) of the title product as a solid HRMS m/z calcd for C11H12N2O2(M)+204.0899, found 204.0906.

Aufarbeitung

  1. extractionextracted with EtOAc
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-857a2678dc564e43936085345f896338
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07071180B2

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