Phosphorus oxychloride → HCID 21882749, compound

HRID 722056Notes

Reaction equation

HRID 722056 reaction equation
O[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([CH2:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:4][N:3]=1.P(Cl)(Cl)([Cl:20])=O.C(=O)([O-])O.[Na+]>>[Cl:20][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([CH2:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 178526518HCID 178526518, compound2×

Product 1

HCID 21882749HCID 21882749, compound

Conditions

Temperature
120 °C

Procedure

A mixture of 1.8 g of 2-hydroxy-3-nitro-5-cyclohexylmethylpyridine (starting material E4) and 13 ml of phosphorous oxychloride is heated under reflux to 120° C. for two 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 1:15). Concentration of the chromatographically pure fractions gives 0.84 g of the title compound as an orange oil.

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 1:15)

Sources & evidence

ORD record
ord-26f0718f239a401889095ffa3a2df465
Source dataset
uspto-grants-2006_11
Patent number
US07138399B2

Reaction notes

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