Triethylamine → 5-(4-Nitrophenoxy)-3-chloropyridine

HRID 2116543Notes

Reaction equation

HRID 2116543 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[Cl:11][C:12]1[CH:13]=[N:14][CH:15]=[C:16]([OH:18])[CH:17]=1.C(N(CC)CC)C>O1CCOCC1>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([O:18][C:16]2[CH:17]=[C:12]([Cl:11])[CH:13]=[N:14][CH:15]=2)=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9590p-FluoronitrobenzeneHCID 5823053-Hydroxy-5-chloropyridine

Product 1

HCID 121093595-(4-Nitrophenoxy)-3-chloropyridineYield 44.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 4-fluoro-nitrobenzene (913 μL, 8.61 mmol, from Aldrich) in dioxane (1 mL) was added 3-chloro-5-hydroxypyridine (558 mg, 4.31 mmol, from Aldrich) followed by triethylamine (661 μL, 4.74 mmol). The solution was refluxed for 4.5 hours, evaporated and the crude solid was dissolved in ethyl acetate. The solution was washed three times with saturated K2CO3 solution, once with brine and then back-extracted with ethyl acetate. The two organic solutions were combined, concentrated and the residue was purified by chromatography (diethyl ether as eluant) to provide 481 mg of the title compound.

Workup

  1. temperatureThe solution was refluxed for 4.5 hours
  2. customevaporated
  3. dissolutionthe crude solid was dissolved in ethyl acetate
  4. washThe solution was washed three times with saturated K2CO3 solution
  5. extractiononce with brine and then back-extracted with ethyl acetate
  6. concentrationconcentrated
  7. customthe residue was purified by chromatography (diethyl ether as eluant)

Sources & evidence

ORD record
ord-40bce66d57ca4b9e820acae772443eec
Source dataset
uspto-grants-2008_10
Patent number
US07439242B2

Reaction notes

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