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

HRID 37468

Reaction equation

HRID 37468 reaction equation
[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

Participants

4

Reactant 2

HCID 69990Phenylphosphonic dichlorideHCID 19935597Diethyl 2-hydroxy-5-nitro-6-phenylpyridine-3,4-dicarboxylate

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

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%).

Workup

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

Sources & evidence

ORD record
ord-c122d6c730f541f4a3dcfbcfd6f66660
Source dataset
uspto-grants-1995_05
Patent number
US05420275

Linked notes

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