Potassium Carbonate → 5-(4,5-dimethyl-1H-imidazol-1-yl)-1,6-naphthyridin-2(1H)-one

HRID 542517Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 542517
Br[C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6](=[O:12])[NH:7]2.C(=O)([O-])[O-].[K+].[K+].[CH3:19][C:20]1[N:21]=[CH:22][NH:23][C:24]=1[CH3:25]>CN(C)C=O>[CH3:19][C:20]1[N:21]=[CH:22][N:23]([C:2]2[N:11]=[CH:10][CH:9]=[C:8]3[C:3]=2[CH:4]=[CH:5][C:6](=[O:12])[NH:7]3)[C:24]=1[CH3:25]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 753064,5-Dimethyl-1H-imidazoleHCID 117758245-Bromo-1,6-naphthyridin-2(1H)-one

Produkt 1

HCID 101056965-(4,5-dimethyl-1H-imidazol-1-yl)-1,6-naphthyridin-2(1H)-oneAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture containing 12.5 g of 5-bromo-1,6-naphthyridin-2(1H)-one, 300 ml of dimethylformamide, 13.8 g of anhydrous potassium carbonate, 10.8 g of 4,5-dimethylimidazole and 200 mg of cuprous bromide was refluxed with stirring for eight hours About 20 ml of the solvent was distilled off using a water separator to remove any moisture from the reaction mixture. The remaining reaction mixture was concentrated on a rotary evaporator. The residue was dissolved in water, acidified with acetic acid and evaporated to dryness on a rotary evaporator. The residue was treated with 50 ml of water and the brown solid was collected, washed with water, recrystallized from ethanol in the presence of decolorizing charcoal. The resulting pale yellow solid was dried at 80°-85° C. to yield 6.4 g of 5-(4,5-dimethyl-1H-imidazol-1-yl)-1,6-naphthyridin-2(1H)-one, m.p. 256°-258° C.

Aufarbeitung

  1. temperaturewas refluxed
  2. distillationwas distilled off
  3. customto remove any moisture from the reaction mixture
  4. customThe remaining reaction mixture
  5. concentrationwas concentrated on a rotary evaporator
  6. dissolutionThe residue was dissolved in water
  7. customevaporated to dryness on a rotary evaporator
  8. additionThe residue was treated with 50 ml of water
  9. customthe brown solid was collected
  10. washwashed with water
  11. customrecrystallized from ethanol in the presence of decolorizing charcoal
  12. customThe resulting pale yellow solid was dried at 80°-85° C.

Quellen und Nachweise

ORD-Eintrag
ord-f29556efb5114a53aa2230b52b7194b0
Quelldatensatz
uspto-grants-1987_04
Patentnummer
US04657915

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