Hydroxyamine hydrochloride → 6-bromo-3,4-dihydro-1H-naphthalen-2-one Oxime

HRID 32078Notes

Reaction equation

HRID 32078 reaction equation
[Br: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].CC([O-])=O.[Na+]>CCO.O>[Br: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 27335536-Bromo-2-tetralone

Product 1

HCID 734461306-bromo-3,4-dihydro-1H-naphthalen-2-one Oxime

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a mixture of 6-bromo-3,4-dihydro-1H-naphthalen-2-one (5.370 g, 23.86 mmol) and hydroxylamine hydrochloride (2.487 g, 35.79 mmol) in EtOH (80 mL) was added a solution of NaOAc (5.871 g, 71.57 mmol) in H2O (20 mL). The mixture was heated to reflux for 2 h. The reaction was cooled to RT and concentrated in vacuo. The residue was suspended in H2O and filtered. The pad was washed with H2O (2×50 mL) and Et2O (2×50 mL) and the solids were dried in vacuo to furnish the title compound, which was used without further purification. MS (APCI pos) 242 (M+H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 h
  3. concentrationconcentrated in vacuo
  4. filtrationfiltered
  5. washThe pad was washed with H2O (2×50 mL) and Et2O (2×50 mL)
  6. customthe solids were dried in vacuo

Sources & evidence

ORD record
ord-5251abb8ef3d4e07a721a91e6cc405c5
Source dataset
uspto-grants-2008_09
Patent number
US07425631B2

Reaction notes

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