Pyridine → 3,5-Dimethyl-4-(4-nitrophenyl)-isoxazole

HRID 450090Notes

Reaction equation

HRID 450090 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([C:14](=O)[CH3:15])[C:11](=[O:13])[CH3:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl.NO.[N:20]1C=CC=CC=1>C(O)C>[CH3:15][C:14]1[C:10]([C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)=[C:11]([CH3:12])[O:13][N:20]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 35304123-(4-Nitrophenyl)pentane-2,4-dione

Product 1

HCID 153732593,5-Dimethyl-4-(4-nitrophenyl)-isoxazoleYield 91.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-(4-nitrophenyl)-pentane-2,4-dione (50 mg, 0.22 mmol), hydroxylamine hydrochloride (15 mg, 0.22 mmol) and pyridine (17 mg, 0.22 mmol) in ethanol (10 ml) was heated to reflux overnight. Evaporation of the solvent gave a residue which was partitioned between water and ethyl acetate. The organic layer was separated, washed with water, then brine and dried. Evaporation to dryness yielded 3,5-dimethyl-4-(4-nitrophenyl)-isoxazole (44 mg, 90%) as solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. customEvaporation of the solvent
  4. customgave a residue which
  5. customwas partitioned between water and ethyl acetate
  6. customThe organic layer was separated
  7. washwashed with water
  8. dry with materialbrine and dried
  9. customEvaporation to dryness

Sources & evidence

ORD record
ord-477b9746117b40318123898ec5ede96c
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Reaction notes

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