Phenylphosphonic dichloride → 3,4-Diethyl 2-chloro-5-nitro-6-phenyl-3,4-pyridinedicarboxylate

HRID 37468

Reaktionsgleichung

[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].C1(P(Cl)([Cl:35])=O)C=CC=CC=1>O>[Cl:35][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

Reaktionsbedingungen

Temperatur: 150 °C

Versuchsvorschrift

To 1.0 g of 3,4-diethoxycarbonyl-5-nitro-6-phenyl-2-pyridone was added 1.3 ml (3.37 eq.) of phenylphosphonic dichloride, and the mixture was heated at 150° C. for 2.5 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of sodium chloride, and dried over magnesium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane 1:2), to give an oily product. Yield: 950 mg (90.5%).

Aufarbeitung

extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with water
dry with materiala saturated aqueous solution of sodium chloride, and dried over magnesium sulfate
distillationThe solvent was distilled off
customthe residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane 1:2)
customto give an oily product

Quellen und Nachweise

ORD-Eintrag: ord-c122d6c730f541f4a3dcfbcfd6f66660
Quelldatensatz: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05420275

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