Formic Acid → 8-nitro-2-ethoxycarbonyl-4-oxo-4H-1-benzopyran

HRID 1603880Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1603880
Br[C:2]1[CH:3]=[C:4]([N+:18]([O-:20])=[O:19])[C:5]2[O:10][C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:8][C:7](=[O:16])[C:6]=2[CH:17]=1.C(O)=O>[Pd].CN(C)C=O>[N+:18]([C:4]1[C:5]2[O:10][C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:8][C:7](=[O:16])[C:6]=2[CH:17]=[CH:2][CH:3]=1)([O-:20])=[O:19]

Komponenten

5

Edukt 2

HCID 284Formic AcidHCID 19606344ethyl 6-bromo-8-nitro-4-oxo-4H-1-benzopyran-2-carboxylate

Produkt 1

HCID 100840998-nitro-2-ethoxycarbonyl-4-oxo-4H-1-benzopyranAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
145 °C

Versuchsvorschrift

A mixture of ethyl 6-bromo-8-nitro-4-oxo-4H-1-benzopyran-2-carboxylate (5.0 g, 14.6 mmol), 10% palladium-on-charcoal (0.541 g), formic acid (7.90 ml) and N,N-dimethylformamide (42 ml) was stirred at 145° C. for 5.75 h under inert atmosphere. After this time the mixture was left to cool and the catalyst was removed by filtration, washing it with N,N-dimethylformamide. The resulting filtrate was evaporated to dryness and the obtained residue was purified by chromatography through a silica gel column. Eluting with hexane:chloroform, 85:15, 2.109 g of the title product were recovered (55% yield).

Aufarbeitung

  1. waitAfter this time the mixture was left
  2. temperatureto cool
  3. customthe catalyst was removed by filtration
  4. washwashing it with N,N-dimethylformamide
  5. customThe resulting filtrate was evaporated to dryness
  6. customthe obtained residue was purified by chromatography through a silica gel column
  7. washEluting with hexane
  8. customchloroform, 85:15, 2.109 g of the title product were recovered (55% yield)

Quellen und Nachweise

ORD-Eintrag
ord-baf5902e322a4a4eb8fd5975cb730954
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05990142

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