Water → 3-(2-Naphthyloxy)-4-nitropyridine-N-oxide

HRID 2106727Notes

Reaction equation

HRID 2106727 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[OH:11].C(=O)([O-])[O-].[Na+].[Na+].F[C:19]1[CH:20]=[N+:21]([O-:28])[CH:22]=[CH:23][C:24]=1[N+:25]([O-:27])=[O:26].O>CN(C)C=O>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][C:19]1[CH:20]=[N+:21]([O-:28])[CH:22]=[CH:23][C:24]=1[N+:25]([O-:27])=[O:26]

Participants

6

Reactant 4

HCID 962WaterHCID 86632-NaphtholHCID 10340Sodium CarbonateHCID 5940283-Fluoro-4-nitropyridin-1-ium-1-olate

Product 1

HCID 150688883-(2-Naphthyloxy)-4-nitropyridine-N-oxide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-naphthol (7 g) in 50 ml dimethylformamide was added sodium carbonate (10 g), followed by 3-fluoro-4-nitropyridine-N-oxide. After stirring three hours at ambient temperature the reaction mixture was stirred with water and extracted with ethyl acetate. The organic extract was washed with water and saturated sodium chloride solution, dried (anhy. MgSO4), filtered and concentrated to a solid. This solid was triturated with ether, collected and dried to give a solid, 11.6 g, m.p. 130°-133° C. A three gram portion was recrystallized from ethanol to give crystals, 2.8 g, m.p. 131°-133° C.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe organic extract
  3. washwas washed with water and saturated sodium chloride solution
  4. customdried (anhy
  5. filtrationMgSO4), filtered
  6. concentrationconcentrated to a solid
  7. customThis solid was triturated with ether
  8. customcollected
  9. customdried
  10. customto give a solid, 11.6 g, m.p. 130°-133° C
  11. customA three gram portion was recrystallized from ethanol
  12. customto give crystals, 2.8 g, m.p. 131°-133° C.

Sources & evidence

ORD record
ord-a2ee704035e249919975bf8879ae2e52
Source dataset
uspto-grants-1990_06
Patent number
US04931457

Reaction notes

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