Water → 3-(4-Nitrophenoxy)pyridine

HRID 1802799Notes

Reaction equation

HRID 1802799 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[OH:11][C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([O:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 74741-Chloro-4-nitrobenzeneHCID 79713-HydroxypyridineHCID 11430Potassium Carbonate

Product 1

HCID 1199023-(4-Nitrophenoxy)pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

1-Chloro-4-nitrobenzene (40 g, 0.25 mol) and 3-hydroxypyridine (36 g, 0.38 mol) were dissolved in N,N-dimethylformamide (100 ml). Potassium carbonate (52.6 g, 0.38 mol) was added, and the mixture was stirred for 20 h at 100° C. Water was added, and the resulting mixture was extracted with ethyl acetate, washed with saturated sodium chloride solution and dried over anhydrous magnesium sulfate to give 3-(4-nitro-phenoxy)-pyridine.

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washwashed with saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-125d821836424ea6a65faec65259cf9b
Source dataset
uspto-grants-2013_01
Patent number
US08349885B2

Reaction notes

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