Hydroxyamine hydrochloride → 6-fluoro-3,4-dihydronaphthalen-2(1H)-one Oxime

HRID 1592334Notes

Reaction equation

HRID 1592334 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][C:7](=O)[CH2:6][CH2:5]2.Cl.[NH2:14][OH:15].C([O-])(=O)C.[Na+]>C(O)C.O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][C:7](=[N:14][OH:15])[CH2:6][CH2:5]2

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 50443856-Fluoro-1,2,3,4-tetrahydronaphthalen-2-one

Product 1

HCID 860515846-fluoro-3,4-dihydronaphthalen-2(1H)-one OximeYield 97%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A solution of 6-fluoro-3,4-dihydronaphthalen-2(1H)-one (W. Adcock, P. D. Bettess, S. Q. A. Rizvi, Aust. J. Chem. 1970, 23, 1921-1937; 1.50 g, 9.13 mmol) in ethanol (10 mL) was treated with hydroxylamine hydrochloride (775 mg, 11.14 mmol), sodium acetate (2.01 g, 14.79 mmol) and water (6 mL) and the mixture was stirred at room temperature for 30 min, during which time a dense precipitate formed. The mixture was diluted with water and extracted with ether. The organic phases were dried and concentrated to provide a yellowish solid (1.58 g, 97%) used without further purification.

Workup

  1. customformed
  2. extractionextracted with ether
  3. customThe organic phases were dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a5f02bfadcd54aec9c514a47f9f81409
Source dataset
uspto-grants-2007_11
Patent number
US07291744B2

Reaction notes

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