Sodium Methoxide → 8-(Benzyloxy)-2-methoxyquinoline

HRID 1782012Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1782012
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([O:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:20][O-:21].[Na+]>C1(C)C=CC=CC=1.CO>[CH2:13]([O:12][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[N:3]=[C:2]([O:21][CH3:20])[CH:11]=[CH:10]2)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

5

Edukt 2

HCID 10942334Sodium MethoxideHCID 220422348-(Benzyloxy)-2-chloroquinoline

Produkt 1

HCID 673664878-(Benzyloxy)-2-methoxyquinolineAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

The crude 2-chloro-8-benzyloxyquinoline from above was dissolved in toluene (10 mL) and added to a stirred 25 wt % solution of NaOMe in MeOH (50 mL). The reaction solution was heated with stirring overnight at 70° C. After cooling to room temperature, the reaction solution was poured onto ice and extracted with toluene. The combined organic extracts were dried (MgSO4) and concentrated in vacuo to give a colorless oil (6.14 g, 92%). The product was used without further purification.

Aufarbeitung

  1. temperatureThe reaction solution was heated
  2. temperatureAfter cooling to room temperature
  3. additionthe reaction solution was poured onto ice
  4. extractionextracted with toluene
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-fa7e0147be2e4f0db41ecde21e4aadae
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07498326B2

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