Potassium Iodide → 3-(Quinolin-4-yloxy)propan-1-ol

HRID 40797

Reaktionsgleichung

Reaktionsgleichung von HRID 40797
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([OH:11])=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Cl[CH2:21][CH2:22][CH2:23][OH:24]>CN(C=O)C>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([O:11][CH2:21][CH2:22][CH2:23][OH:24])=[CH:3][CH:2]=1

Komponenten

6

Edukt 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 123133-Chloro-1-propanolHCID 178516385quinolin-4-ol

Produkt 1

HCID 685762503-(Quinolin-4-yloxy)propan-1-olAusbeute 28 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

A suspension of quinolin-4-ol (1.35 g, 9.30 mmol), anhydrous potassium carbonate (3.73 g, 26 mmol) and potassium iodide (4.23 g) in anhydrous DMF (8 mL) was stirred at 25° C. for 30 minutes. 3-Chloropropanol (2.93 g, 31 mmol) was added and the reaction was stirred until the starting material was consumed. The reaction was diluted with dichloromethane and extracted with water. The product was obtained as a slightly yellow solid (0.5298 g, 28%) after evaporation of the dichloromethane layer, and was used for the next step without further purification. 1H NMR (400 MHz, CDCl3): 2.09 (2H, m), 3.93 (2H, t, J=5.6 Hz), 4.10 (2H, t, J=5.6 Hz), 4.51 (11H, s), 6.25 (1H, d, J=5.5 Hz), 7.32 (1H, t, J=7.4 Hz), 7.56 (1H, t, J=8.2 Hz), 7.90 (1H, d, J=8.4 Hz), 7.93 (1H, d, J=8.4 Hz), 8.36 (1H, d, J=5.3 Hz).

Aufarbeitung

  1. stirringthe reaction was stirred until the starting material
  2. customwas consumed
  3. additionThe reaction was diluted with dichloromethane
  4. extractionextracted with water

Quellen und Nachweise

ORD-Eintrag
ord-d91781c33a6f4b49b78e7d1ae719acf2
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530491B2

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