Phenol → HCID 23025756, compound

HRID 1437465Notes

Reaction equation

HRID 1437465 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH2:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][CH:3]=1.[C:12]1([OH:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C[O-].[Na+]>C(#N)C>[N+:9]([C:5]1[C:6]([NH2:8])=[N:7][C:2]([O:18][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:3][CH:4]=1)([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 996PhenolHCID 27240356-Chloro-3-nitropyridin-2-ylamineHCID 10942334Sodium Methoxide

Product 1

HCID 23025756HCID 23025756, compoundYield 68.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

6-Chloro-3-nitro-2-pyridine amine (1.2 g), phenol (3.1 g) and sodium methoxide (0.4 g) were dissolved in acetonitrile (20 ml), and the solution was heated for 12 hours under reflux. After the completion of the reaction, the solvent was distilled off under reduced pressure. The residue was distributed into ethyl acetate and a saturated aqueous solution of sodium bicarbonate. The organic layer was washed with water and dried over MgSO4. The solvent was distilled off under reduced pressure, and the residue was subjected to silica gel column chromatography. The fraction eluted with ethyl acetate-hexane (1:10, v/v) was concentrated under reduced pressure. The resulting crystals were collected by filtration to obtain 3-nitro-6-phenoxy-2-pyridine amine (1.1 g, 66%).

Workup

  1. temperaturethe solution was heated for 12 hours
  2. temperatureunder reflux
  3. customAfter the completion of the reaction
  4. distillationthe solvent was distilled off under reduced pressure
  5. washThe organic layer was washed with water
  6. dry with materialdried over MgSO4
  7. distillationThe solvent was distilled off under reduced pressure
  8. washThe fraction eluted with ethyl acetate-hexane (1:10
  9. concentrationv/v) was concentrated under reduced pressure
  10. filtrationThe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-b236fc554130430387246e02487fe830
Source dataset
uspto-grants-2009_11
Patent number
US07622479B2

Reaction notes

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