4-Fluorophenol → 4-(4-Fluorophenoxy)-1,5-naphthyridine

HRID 2255361Notes

Reaction equation

HRID 2255361 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][N:10]=2)[N:5]=[CH:4][CH:3]=1.[F:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1>C(OCC)(=O)C.[OH-].[Na+]>[F:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][N:10]=3)[N:5]=[CH:4][CH:3]=2)=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 97324-FluorophenolHCID 5962624-Chloro-1,5-naphthyridine

Product 1

HCID 197378694-(4-Fluorophenoxy)-1,5-naphthyridineYield 47.1%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture comprising 150 mg (0.911 mmole) of 4-chloro-1,5-naphthyridine and 1.00 g of 4-fluorophenol was heated at 160° C. After one hour, the mixture was cooled and dissolved in ethyl acetate and 2N sodium hydroxide. The organic layer was washed twice with base to remove excess 4-fluorophenol. The organic layer was then dried with magnesium sulfate and concentrated, producing an oil that slowly crystallized. This product was recrystallized in heptane, giving 103 mg of the title product. MP 122°-124° C. Yield 47%.

Workup

  1. temperaturethe mixture was cooled
  2. washThe organic layer was washed twice with base
  3. customto remove excess 4-fluorophenol
  4. dry with materialThe organic layer was then dried with magnesium sulfate
  5. concentrationconcentrated
  6. customproducing an oil that
  7. customslowly crystallized
  8. customThis product was recrystallized in heptane

Sources & evidence

ORD record
ord-4a9ff2caa72f492a8f9c458e6cc984e4
Source dataset
uspto-grants-1993_08
Patent number
US05240916

Reaction notes

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