Phosphorus oxychloride → HCID 21882768, compound

HRID 722061Notes

Reaction equation

HRID 722061 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([N+:15]([O-:17])=[O:16])[C:11](O)=[N:12][CH:13]=2)=[CH:4][CH:3]=1.C(=O)([O-])O.[Na+].P(Cl)(Cl)([Cl:25])=O>>[Cl:25][C:11]1[C:10]([N+:15]([O-:17])=[O:16])=[CH:9][C:8]([C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=2)=[CH:13][N:12]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 178526452HCID 178526452, compound

Product 1

HCID 21882768HCID 21882768, compound

Conditions

Temperature
120 °C

Procedure

A mixture of 10.2 g of 5-(4-bromphenyl)-2-hydroxy-3-nitropyridine (starting material H4) and 40 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 (ethyl acetate/petroleum ether 1:12). Concentration of the chromatographically pure fractions gives 1.52 g of the title compound as yellow crystals of m.p. 116–117° C. The mass spectrum shows the molecular peak M+ at 314 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 (ethyl acetate/petroleum ether 1:12)

Sources & evidence

ORD record
ord-ef8f2b4c9bb84c6e81310eb8eee703fa
Source dataset
uspto-grants-2006_11
Patent number
US07138399B2

Reaction notes

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