Hydroxyamine hydrochloride → HCID 85069309, compound

HRID 1636891Notes

Reaction equation

HRID 1636891 reaction equation
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=[CH:3][C:2]=1[C:14](=O)[C:15]([F:21])([F:20])[CH2:16][C:17]([OH:19])=[O:18].C([O-])(=O)C.[Na+].Cl.[NH2:29][OH:30]>CO.O>[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=[CH:3][C:2]=1[C:14](=[N:29][OH:30])[C:15]([F:21])([F:20])[CH2:16][C:17]([OH:19])=[O:18]

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 9882907HCID 9882907, compound

Product 1

HCID 85069309HCID 85069309, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 4-dibenzofuran-2-yl-3,3-difluoro-4-oxo-butyric acid (1 equivalent, Example 1) and sodium acetate (1.2 equivalents) in methanol is treated with a solution of hydroxylamine hydrochloride (1.2 equivalents) in water. The solution is heated to reflux for 3 hours, then cooled, concentrated, and filtered. The filter cake is washed with water and dried in vacuo. The crude product is recrystallized from an organic solvent, such as ethyl acetate, to give the title compound.

Workup

  1. temperatureThe solution is heated
  2. temperatureto reflux for 3 hours
  3. temperaturecooled
  4. concentrationconcentrated
  5. filtrationfiltered
  6. washThe filter cake is washed with water
  7. customdried in vacuo
  8. customThe crude product is recrystallized from an organic solvent, such as ethyl acetate

Sources & evidence

ORD record
ord-8a4156a8262349a1aea01991fa87a2af
Source dataset
uspto-grants-2000_03
Patent number
US06037361

Reaction notes

Loading…