Ammonia → 3-Benzyloxypyrid-4-one

HRID 481464Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 481464
[CH2:1]([O:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12]O[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH3:16]>>[CH2:1]([O:8][CH:9]1[C:14](=[O:15])[CH:13]=[CH:12][N:16]=[CH:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

3

Edukt 2

HCID 222AmmoniaHCID 108996783-Benzyloxy-4-pyrone

Produkt 1

HCID 689255013-Benzyloxypyrid-4-one

Versuchsvorschrift

This method is adapted from that of Bartulin et al., J. Heterocyclic Chem. 29:1017-1019 (1992), which is hereby incorporated by reference. A 3-benzyloxy-4-pyrone, prepared as in Method B, is added to an ethanolic solution of aqueous ammonia. The reaction mixture is stirred for approximately 3 days, concentrated under reduced pressure, triturated with acetone, and the solid recrystallized from ethanol to yield the corresponding 3-benzyloxypyrid-4-one. To a solution of this pyrid-4-one in aqueous ethanol containing one equivalent of sodium hydroxide was added an equivalent of n-alkyl bromide. The reaction mixture was heated under reflux for 24 hours after which it was cooled, concentrated under reduced pressure, and extracted with an appropriate solvent. After washing, the organic phase with water, it is dried over magnesium sulfate. The product is obtained upon concentration of the solution under reduced pressure. Crude 1-alkyl-3-benzyloxypyrid-4-one in acetic acid containing 40% hydrobromic acid is then heated on a steam bath for 30 minutes. The 1-alkyl-3-hydroxypyrid-4-one precipitates and is subsequently recrystallized from benzene in good yield with a narrow melting point and appropriate NMR spectrum. ##STR6##

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. customtriturated with acetone
  3. customthe solid recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-6d36347b12514cb5ac1dea8c108c3996
Quelldatensatz
uspto-grants-1998_08
Patentnummer
US05789426

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