Ethanol → 4-Ethoxyquinolin-8-amine

HRID 1469783Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1469783
[H-].[Na+].Cl[C:4]1[C:13]2[C:8](=[C:9]([NH2:14])[CH:10]=[CH:11][CH:12]=2)[N:7]=[CH:6][CH:5]=1.[CH2:15]([OH:17])[CH3:16]>>[CH2:15]([O:17][C:4]1[C:13]2[C:8](=[C:9]([NH2:14])[CH:10]=[CH:11][CH:12]=2)[N:7]=[CH:6][CH:5]=1)[CH3:16]

Komponenten

4

Edukt 3

HCID 702EthanolHCID 24758Sodium hydrideHCID 126042744-Chloroquinolin-8-amine

Produkt 1

HCID 682812844-Ethoxyquinolin-8-amine

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a solution of ethanol (5 mL) was added NaH (141 mg, 5.6 mmol, 95%) at 0° C. and the reaction mixture was stirred at rt for 30 min. before 4-chloroquinolin-8-amine (200 mg, 1.12 mmol) was added to the reaction mixture. Then the reaction mixture was heated in a sealed tube at 110° C. for 12 h before it was quenched with 1N HCl. Then the reaction mixture was extracted with chloroform and the organic layer was washed with brine, separated, dried, filtered and concentrated. The residue was purified by column chromatography to afford 140 mg of the title product. MS [M+H]+: 189.15.

Aufarbeitung

  1. additionwas added to the reaction mixture
  2. customwas quenched with 1N HCl
  3. extractionThen the reaction mixture was extracted with chloroform
  4. washthe organic layer was washed with brine
  5. customseparated
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-01231f72cbe841a5af7d5c1b193ca28b
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09006257B2

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