Water → 3-(4-Nitrophenoxy)pyridine

HRID 1876305Notes

Reaction equation

HRID 1876305 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 thereto, and the mixture was stirred for 20 h at 100° C. Water was added to the reaction solution, which was then extracted with ethyl acetate. The extract was washed with saturated sodium chloride solution, and dried over anhydrous magnesium sulfate to give 3-(4-nitro-phenoxy)-pyridine.

Workup

  1. extractionwas then extracted with ethyl acetate
  2. washThe extract was washed with saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-306411f1a45a4b358b039866a2f0c5eb
Source dataset
uspto-grants-2012_11
Patent number
US08309586B2

Reaction notes

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