Hydroxyamine hydrochloride → HCID 72363102, compound

HRID 2074173Notes

Reaction equation

HRID 2074173 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[O:10][CH2:9][CH2:8][C:7]2=O.Cl.[NH2:14][OH:15].C([O-])(=O)C.[Na+]>>[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[O:10][CH2:9][CH2:8][C:7]2=[N:14][OH:15]

Participants

4

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 139538178-Fluoro-2,3-dihydro-4H-1-benzopyran-4-one

Product 1

HCID 72363102HCID 72363102, compound

Procedure

A round bottom flask was charged with 8-fluorochroman-4-one (8.2 g), hydroxylamine hydrochloride (3.78 g) and sodium acetate (4.46 g). A reflux condenser was added, the flask was purged with argon, dry EtOH (20 mL) was added, and the mixture was stirred at reflux for 18 hours. The solution was cooled to room temperature, diluted with EtOAc, and washed with water. The organic phase was dried, and evaporated to give the intermediate 8-fluorochroman-4-one oxime (4), which was reduced with Raney Nickel in EtOH at 50 PSI to yield the title amine (5) (4.69 g, 57%).

Workup

  1. additionA reflux condenser was added
  2. customthe flask was purged with argon, dry EtOH (20 mL)
  3. additionwas added
  4. temperatureat reflux for 18 hours
  5. additiondiluted with EtOAc
  6. washwashed with water
  7. customThe organic phase was dried
  8. customevaporated

Sources & evidence

ORD record
ord-6bd22f95ba2d4fb38a392d3771d5c90f
Source dataset
uspto-grants-2011_04
Patent number
US07919490B2

Reaction notes

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