Potassium Carbonate → 6,7-Dimethoxy-4-(5-nitro-pyridin-2-yloxy)-quinoline

HRID 387745

Reaktionsgleichung

Reaktionsgleichung von HRID 387745
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[NH:9][CH:8]=[CH:7][C:6]2=[O:15].Br[C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][N:18]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][N:18]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 782402-Bromo-5-nitropyridineHCID 4596116,7-Dimethoxy-4-hydroxyquinoline

Produkt 1

HCID 229362516,7-Dimethoxy-4-(5-nitro-pyridin-2-yloxy)-quinolineAusbeute 34,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

6,7-Dimethoxy-1,4-dihydro-4-quinolinone (4.10 g, 20.0 mmol), 2-bromo-5-nitropyridine (4.46 g, 22.0 mmol) and potassium carbonate (5.53 g, 40.0 mmol) were heated and stirred at 70° C. for 3 hours in N,N-dimethylformamide (20 ml). The reaction solution was diluted with ethyl acetate, the insoluble portion was filtered off, and after washing with water and saturated saline and drying the organic layer over anhydrous magnesium sulfate, the drying agent was filtered off and the filtrate was distilled off under reduced pressure. The obtained crude product was subjected to silica gel column chromatography (eluent: ethyl acetate), and the fraction containing the target substance was concentrated, suspended in ethyl acetate and diluted with hexane, after which the crystals were filtered out, washed with hexane and then blow-dried to obtain the title compound (2.23 g, 6.81 mmol, 34%) as yellow crystals.

Aufarbeitung

  1. filtrationthe insoluble portion was filtered off
  2. washafter washing with water and saturated saline
  3. dry with materialdrying the organic layer over anhydrous magnesium sulfate
  4. filtrationthe drying agent was filtered off
  5. distillationthe filtrate was distilled off under reduced pressure
  6. customThe obtained crude product
  7. additionthe fraction containing the target substance
  8. concentrationwas concentrated
  9. additiondiluted with hexane
  10. filtrationafter which the crystals were filtered out
  11. washwashed with hexane
  12. customblow-dried

Quellen und Nachweise

ORD-Eintrag
ord-f00eee7b12e14240881234f9afacc957
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372981B2

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