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

HRID 542512Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 542512
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.[CH3:13][C:14]1[NH:15][CH:16]=[CH:17][N:18]=1.CN1CCCC1=O.C(=O)([O-])[O-].[K+].[K+]>[Cu].C(O)(=O)C.O>[CH3:13][C:14]1[N:15]([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)[CH:16]=[CH:17][N:18]=1

Komponenten

8

Edukt 4

HCID 11430Potassium CarbonateHCID 127492-MethylimidazoleHCID 13387N-methyl-2-pyrrolidoneHCID 117758245-Bromo-1,6-naphthyridin-2(1H)-one

Produkt 1

HCID 100139235-(2-methyl-1H-imidazol-1-yl)-1,6-naphthyridin-2(1H)-oneAusbeute 42,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23978CopperKatalysatorHCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture containing 5.6 g of 5-bromo-1,6-naphthyridin-2(1H)-one, 8 g of 2-methyl-1H-imidazole, 25 ml of N-methylpyrrolidinone, 3.4 g of anhydrous potassium carbonate and 50 mg of copper powder was refluxed for 6 hours, allowed to cool to room temperature and then poured into 100 ml of water. The resulting solution was neutralized by adding acetic acid and the resulting solution was allowed to stand overnight at room temperature. The solid that separated was collected, recrystallized from dimethylformamide and dried in a vacuum oven at 90°-95° C. to yield 2.4 g of 5-(2-methyl-1H-imidazol-1-yl)-1,6-naphthyridin-2(1H)-one, m.p. >310° C.

Aufarbeitung

  1. temperaturewas refluxed for 6 hours
  2. customThe solid that separated
  3. customwas collected
  4. customrecrystallized from dimethylformamide
  5. customdried in a vacuum oven at 90°-95° C.

Quellen und Nachweise

ORD-Eintrag
ord-65cccba43bfb40fe83e9688528f493c5
Quelldatensatz
uspto-grants-1987_04
Patentnummer
US04657915

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