Water → (8-Methoxyquinolin-5-yl)methanol

HRID 2374166Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2374166
[OH:1][CH2:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][C:7](O)=[N:8]2.[C:14](=O)([O-])[O-:15].[K+].[K+].CI.O>CN(C=O)C>[OH:1][CH2:2][C:3]1[CH:12]=[CH:11][C:10]([O:15][CH3:14])=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[N:8]2

Komponenten

6

Edukt 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178519443HCID 178519443, Verbindung

Produkt 1

HCID 7172171(8-Methoxyquinolin-5-yl)methanolAusbeute 90,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

5-(Hydroxymethyl) quinolinol (6.7 g, 38 mmol) was dissolved in DMF (38 mL) and treated with potassium carbonate (16 g, 116 mmol) followed by methyl iodide (2.9 mL, 6.8 g, 48 mmol). The mixture was allowed to stir overnight at RT, then poured into a separatory funnel with water and extracted 3× DCM. The organic layer was dried over Na2SO4, and concentrated to give solid 5-hydroxymethyl-8-methoxyquinoline (6.5 g). 1H NMR (CDCl3) δ 8.97 (d, 1H), 8.51 (d, 1H) 7.49 (m, 2H), 6.99 (d, 1H), 5.05 (s, 2H), 4.09 (s, 3H).

Aufarbeitung

  1. extractionextracted 3× DCM
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-2172f9bda830476993ec08712e0f5d53
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07462600B2

Notizen zur Reaktion

Wird geladen…