Water → HCID 69252831, Verbindung

HRID 2222296Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2222296
[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([OH:12])=[CH:7][CH:6]=2.C(=O)([O-])[O-].[K+].[K+].Br[CH:20]([CH2:30][CH3:31])[C:21]([NH:23][C:24]([CH3:29])([CH3:28])[C:25]#[C:26][CH3:27])=[O:22].O>CN(C)C=O.CCCCCC.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:12][CH:20]([CH2:30][CH3:31])[C:21]([NH:23][C:24]([CH3:29])([CH3:28])[C:25]#[C:26][CH3:27])=[O:22])=[CH:7][CH:6]=2

Komponenten

7

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 148078713-Bromoquinolin-6-olHCID 210784062-bromo-N-(4-methylpent-2-yn-4-yl)butyramide

Produkt 1

HCID 69252831HCID 69252831, VerbindungAusbeute 40,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 21226206Ethyl acetate hexaneLösungsmittel

Versuchsvorschrift

To a stirred mixture of 3-bromo-6-hydroxyquinoline (0.179 g) and anhydrous potassium carbonate (0.121 g) in dry N,N-dimethylformamide (2 ml) at 80° C. was added 2-bromo-N-(4-methylpent-2-yn-4-yl) butyramide (0.197 g) and the reaction maintained at this temperature for 15 hours. The brown suspension produced was cooled to ambient temperature, poured into water and extracted with diethyl ether. The extract was washed with water, dried over magnesium sulphate then evaporated under reduced pressure to give a brown gum. The gum was fractionated by chromatography (silica; hexane/ethyl acetate) to give 2-(3-bromo-6-quinolinyloxy)-N-(4-methylpent-2-yn-4-yl) butyramide (0.125 g) as a colourless solid, m.p. 109-12° C., 1H NMR (CDCl3) δ: 1.08(3H, t); 1.58 (3H, s); 1.59(3H, s); 1.77(3H, s); 1.99-2.06(2H, m); 4.54(1H, t); 6.37(1H, s); 7.02(1H, m); 7.42(1H, dd); 8.02(1H, d); 8.19(1H, m); 8.78(1H, m).

Aufarbeitung

  1. temperaturethe reaction maintained at this temperature for 15 hours
  2. customThe brown suspension produced
  3. extractionextracted with diethyl ether
  4. washThe extract was washed with water
  5. dry with materialdried over magnesium sulphate
  6. customthen evaporated under reduced pressure
  7. customto give a brown gum

Quellen und Nachweise

ORD-Eintrag
ord-e8c2e3373c3f4541af3a9cf141b2259f
Quelldatensatz
uspto-grants-2008_05
Patentnummer
US07371764B2

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