Phosphorus oxychloride → HCID 19935610, compound

HRID 37483Notes

Reaction equation

HRID 37483 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][C:23]([O:26][CH3:27])=[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].P(Cl)(Cl)([Cl:31])=O.C(=O)([O-])O.[Na+]>CN(C=O)C>[Cl:31][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][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[N:8]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 199356143,4-Diethoxycarbonyl-6-(4-methoxyphenyl)-5-nitro-2(1H)pyridone

Product 1

HCID 19935610HCID 19935610, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Conditions

Temperature
100 °C

Procedure

To 300 mg of 3,4-diethoxycarbonyl-6-(4-methoxyphenyl)-5-nitro-2(1H)pyridone were added 0.5 ml of phosphorus oxychloride and two drops of DMF. The mixture was heated at 100° C. for 1 hour. After ice water was added, the mixture was neutralized with sodium hydrogencarbonate, followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of sodium chloride and dried. The solvent was distilled off. The residue was purified by silica gel column chromatography (eluent:ethyl acetate/hexane 1:1).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materiala saturated aqueous solution of sodium chloride and dried
  4. distillationThe solvent was distilled off
  5. customThe residue was purified by silica gel column chromatography (eluent:ethyl acetate/hexane 1:1)

Sources & evidence

ORD record
ord-267f4a4c64be4094bf7e33962104fd3f
Source dataset
uspto-grants-1995_05
Patent number
US05420275

Reaction notes

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