Dimethylformamide → 2-Chloro-3,4-diethoxycarbonyl-5-nitro-6-phenylpyridine

HRID 37497

Reaktionsgleichung

Reaktionsgleichung von HRID 37497
[CH2:1]([O:3][C:4]([C:6]1[C:7](=O)[NH:8][C:9]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:10]([N+:17]([O-:19])=[O:18])[C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:5])[CH3:2].CN(C=O)C.P(Cl)(Cl)([Cl:34])=O>>[Cl:34][C:7]1[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:10]([N+:17]([O-:19])=[O:18])=[C:9]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:8]=1

Komponenten

4

Edukt 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 19935597Diethyl 2-hydroxy-5-nitro-6-phenylpyridine-3,4-dicarboxylate

Produkt 1

HCID 199355872-Chloro-3,4-diethoxycarbonyl-5-nitro-6-phenylpyridine

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

In 6.5 ml of phosphorus oxychloride was dissolved 2.5 g of 3,4-diethoxycarbonyl-5-nitro-6-phenyl-2pyridone, followed by addition of 1 ml of DMF. The mixture was heated at 100° C. for 30 minutes. After the reaction mixture was concentrated under reduced pressure, an aqueous solution of sodium hydrogencarbonate was added to the residue for neutralization, followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. After the solvent was distilled off, the residue was subjected to silica gel column chromatography (eluent:ethyl acetate/hexane 1:2), to give 1.9 g of the title compound as yellow needles.

Aufarbeitung

  1. concentrationAfter the reaction mixture was concentrated under reduced pressure
  2. additionan aqueous solution of sodium hydrogencarbonate was added to the residue for neutralization
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materiala saturated aqueous solution of sodium chloride and dried over magnesium sulfate
  6. distillationAfter the solvent was distilled off

Quellen und Nachweise

ORD-Eintrag
ord-e1042bcf07c04ef68cc62404a8ba4b14
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05420275

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