Phenol → 3-Nitro-2-phenoxypyridine

HRID 1601138Notes

Reaction equation

HRID 1601138 reaction equation
[H-].[Na+].[C:3]1([OH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CN(C)C=O.Cl[C:16]1[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][CH:19]=[CH:18][N:17]=1>O>[N+:22]([C:21]1[C:16]([O:9][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)=[N:17][CH:18]=[CH:19][CH:20]=1)([O-:24])=[O:23]

Participants

6

Reactant 4

HCID 996PhenolHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 796132-Chloro-3-nitropyridine

Product 1

HCID 9018963-Nitro-2-phenoxypyridineYield 12.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

3.6 g (150 mmol) of sodium hydride were added, a little at a time, to a mixture of 12 g (128 mmol) of phenol and 100 ml of dimethylformamide. After the evolution of gas had ceased, the resulting mixture was treated with 18 g (114 mmol) of 2-chloro-3-nitropyridine. After the reaction mixture had been stirred at room temperature (approximately 25° C.) for 3 hours, it was treated with water. Following extraction with tert-butyl methyl ether, washing and drying the organic phase and removal of the solvent under reduced pressure, the product crystallized out. It was purified further by stirring with tert-butyl methyl ether/n-pentane. This gave 6.6 g (27%) of the title compound. A further 3.0 g (12%) of the title compound were obtained from the mother liquor.

Workup

  1. extractionextraction with tert-butyl methyl ether
  2. washwashing
  3. customdrying
  4. customthe organic phase and removal of the solvent under reduced pressure
  5. customthe product crystallized out
  6. customIt was purified further
  7. stirringby stirring with tert-butyl methyl ether/n-pentane

Sources & evidence

ORD record
ord-e6060c1b4aac43b2b310e49ab19ecec5
Source dataset
uspto-grants-1999_11
Patent number
US05977146

Reaction notes

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