Phosphorus oxychloride → HCID 21882743, compound

HRID 722059Notes

Reaction equation

HRID 722059 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[C:11]([N+:16]([O-:18])=[O:17])[C:12](O)=[N:13][CH:14]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].C(=O)([O-])O.[Na+].P(Cl)(Cl)([Cl:26])=O>>[Cl:26][C:12]1[C:11]([N+:16]([O-:18])=[O:17])=[CH:10][C:9]([C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)=[CH:14][N:13]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 178526454HCID 178526454, compound

Product 1

HCID 21882743HCID 21882743, compound

Conditions

Temperature
120 °C

Procedure

A mixture of 1.6 g of 5-(3,4-dichlorphenyl)-2-hydroxy-3-nitropyridine (starting material G4) and 10 ml of phosphorous oxychloride is heated under reflux to 120° C. for 3 hours. After cooling the mixture is carefully added to ice/water, then neutralized with sodium hydrogencarbonate and extracted three times with ethyl acetate. The combined organic phases are evaporated to dryness and the residue is chromatographed on a silica gel column (ethylacetate/petroleum ether 1:20). Concentration of the chromatographically pure fractions gives 0.88 g of the title compound as yellow crystals. The mass spectrum shows the molecular peak M+ at 302 Da.

Workup

  1. temperatureis heated
  2. temperatureAfter cooling the mixture
  3. extractionextracted three times with ethyl acetate
  4. customThe combined organic phases are evaporated to dryness
  5. customthe residue is chromatographed on a silica gel column (ethylacetate/petroleum ether 1:20)

Sources & evidence

ORD record
ord-804c4fc937644d2a92b4e849075c8f1f
Source dataset
uspto-grants-2006_11
Patent number
US07138399B2

Reaction notes

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