Ethyl Acetate → 1-(3-(Diethoxyphosphoryl)propyl)-6-methoxy-2-methylquinolinium bromide

HRID 446045

Reaktionsgleichung

Reaktionsgleichung von HRID 446045
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([CH3:13])[CH:7]=[CH:6]2.[CH2:14]([O:16][P:17]([CH2:22][CH2:23][CH2:24][Br:25])(=[O:21])[O:18][CH2:19][CH3:20])[CH3:15].C(OCC)(=O)C>CN(C=O)C>[Br-:25].[CH2:19]([O:18][P:17]([CH2:22][CH2:23][CH2:24][N+:9]1[C:10]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:12][CH:11]=2)[CH:6]=[CH:7][C:8]=1[CH3:13])([O:16][CH2:14][CH3:15])=[O:21])[CH3:20]

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 706486-MethoxyquinaldineHCID 283500Diethyl (3-bromopropyl)phosphonate

Produkt 1

HCID 866399741-(3-(Diethoxyphosphoryl)propyl)-6-methoxy-2-methylquinolinium bromideAusbeute 67,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

A mixture of 6-methoxy-2-methylquinoline (1.0 g, 5.8 mmol) and diethyl-(3-bromopropyl)-phosphonate (1.6 g, 6.4 mmol) was heated in a pressure tube at 140° C. for 16 hours. The mixture was allowed to cool to room temperature, and the resulting mass was dissolved in DMF (4 mL). The combined mixture was then added dropwise to ethyl acetate (40 mL). Precipitated purple solid was collected by centrifugation, washed with ethyl acetate (3×40 mL) and dried under vacuum to yield 1.7 g of Compound 13 which was then used without any further purification. The structure of Compound 13 is given below:

Aufarbeitung

  1. temperatureto cool to room temperature
  2. customPrecipitated purple solid
  3. customwas collected by centrifugation
  4. washwashed with ethyl acetate (3×40 mL)
  5. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-4b005a1688a141d0ad44724d369ee2cb
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476443B2

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