4-Methoxyphenol → HCID 23372923, compound

HRID 1899692Notes

Reaction equation

HRID 1899692 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.[NH2:12][C:13]1[O:17][N:16]=[C:15]([CH3:18])[C:14]=1Br.[OH-].[Na+]>CN(C)C=O.C(OCC)(=O)C>[NH2:12][C:13]1[O:17][N:16]=[C:15]([CH3:18])[C:14]=1[O:11][C:8]1[CH:9]=[CH:10][C:5]([O:4][CH3:3])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 90154-MethoxyphenolHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 104875194-Bromo-3-methylisoxazol-5-amine

Product 1

HCID 23372923HCID 23372923, compoundYield 53.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of sodium hydride (60% dispersion in mineral oil, 52 mg, 1.3 mmol) in dry dimethylformamide (2.0 ml) was added 4-methoxyphenol (0.15 g, 1.2 mmol). After stirring the solution at room temperature of 10 min, 5-amino-4-bromo-3-methylisoxazole (0.20 g, 1.1 mmol) was added, followed by bis(triphenylphosphine)palladium(11) chloride (79 mg, 0.11 mmol). The mixture was heated to 50° C. for 2.5 h and then cooled to room temperature. The dark brown reaction mixture was worked up with ethyl acetate and 5% NaOH. The organic layer was dried with magnesium sulfate, filtered and concentrated under reduced pressure. The residue was chromatographed on silica gel using 20% ethyl acetate in hexanes as eluent to give 0.13 g (51% yield) of 5-amino-4-(4-methoxyphenoxy)-3-methylisoxazole.

Workup

  1. temperatureThe mixture was heated to 50° C. for 2.5 h
  2. temperaturecooled to room temperature
  3. dry with materialThe organic layer was dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was chromatographed on silica gel using 20% ethyl acetate in hexanes as eluent

Sources & evidence

ORD record
ord-ad1b603aa512412bbb524b88809e393b
Source dataset
uspto-grants-1996_11
Patent number
US05571821

Reaction notes

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