Water → 6-nitro-2,2-dimethyl-3-(trifluoroacetamido)methyl-3,4-dihydro-3-hydroxy-4-(2-oxo-1,2-dihydropyridin-1-yl)-2H-1-benzopyran

HRID 2399320Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2399320
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][C:11]([CH3:14])([CH3:13])[C:10]3([CH2:16][NH:17][C:18](=[O:23])[C:19]([F:22])([F:21])[F:20])[O:15][CH:9]3[C:8]=2[CH:24]=1)([O-:3])=[O:2].[NH:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]1=[O:31].O.C(OCC)(=O)C>O1CCOCC1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][C:11]([CH3:14])([CH3:13])[C:10]([CH2:16][NH:17][C:18](=[O:23])[C:19]([F:22])([F:20])[F:21])([OH:15])[CH:9]([N:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]3=[O:31])[C:8]=2[CH:24]=1)([O-:3])=[O:2]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 88712-PyridoneHCID 19386922HCID 19386922, Verbindung

Produkt 1

HCID 193871146-nitro-2,2-dimethyl-3-(trifluoroacetamido)methyl-3,4-dihydro-3-hydroxy-4-(2-oxo-1,2-dihydropyridin-1-yl)-2H-1-benzopyranAusbeute 19,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of 6-nitro-2,2-dimethyl-3-(trifluoroacetamido)methyl-3,4-dihydro-3,4-epoxy-2H-1-benzopyran (0.4 g, 1.16 mmol), 2(1H)-pyridinone (0.22 g, 2.32 mmol) and Triton B (0.05 ml) in dioxane (3 ml) was heated at reflux for nineteen hours. Water and ethyl acetate were added, and the organic phase separated and evaporated under reduced pressure. The residue was chromatographed on silica gel, eluting with dichloromethane/acetone (95/5), to give 0.1 g of 6-nitro-2,2-dimethyl-3-(trifluoroacetamido)methyl-3,4-dihydro-3-hydroxy-4-(2-oxo-1,2-dihydropyridin-1-yl)-2H-1-benzopyran, m.p. 158° C.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for nineteen hours
  3. customthe organic phase separated
  4. customevaporated under reduced pressure
  5. customThe residue was chromatographed on silica gel
  6. washeluting with dichloromethane/acetone (95/5)

Quellen und Nachweise

ORD-Eintrag
ord-02a472cae00649f29d0dd8226bffa9c1
Quelldatensatz
uspto-grants-1995_09
Patentnummer
US05447943

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