Hydroxyamine hydrochloride → 4-Fluoro-2-(5-isoxazolyl)phenol

HRID 1272200Notes

Reaction equation

HRID 1272200 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH:7]=[CH:6][C:5]2=[O:12].Cl.[NH2:14]O>C(O)C>[F:1][C:2]1[CH:11]=[CH:10][C:9]([OH:8])=[C:4]([C:5]2[O:12][N:14]=[CH:7][CH:6]=2)[CH:3]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 6888926-Fluorochromone

Product 1

HCID 27589854-Fluoro-2-(5-isoxazolyl)phenolYield 12%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product from above (6-fluorochromen-4-one (5.25 g, 32.0 mmol) and hydroxylamine hydrochloride (4.65 g, 67.2 mmol) are dissolved in ethanol (180 ml) and the resulting mixture is heated to reflux. The reaction is allowed to stir for 18 hours before cooling and concentrating. The residue is taken up in toluene and filtered to give 690 mg of 4-fluoro-2-isoxazol-5-yl-phenol and from the filtrate 594 mg of 4-fluoro-2-isoxazol-3-yl-phenol.

Workup

  1. temperaturethe resulting mixture is heated to reflux
  2. temperaturebefore cooling
  3. concentrationconcentrating
  4. filtrationfiltered

Sources & evidence

ORD record
ord-4ac770502896430e878b8a40f36d127a
Source dataset
uspto-grants-2007_04
Patent number
US07208505B2

Reaction notes

Loading…