Hydroxyamine hydrochloride → 2a,3,4,5-tetrahydro-2H-acenaphthylen-1-one oxime

HRID 331229Notes

Reaction equation

HRID 331229 reaction equation
[C:1]1(=O)[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][CH2:4][CH:3]3[CH2:2]1.Cl.[NH2:15][OH:16].C([O-])(=O)C.[Na+]>O.C1COCC1.CO>[C:1]1(=[N:15][OH:16])[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][CH2:4][CH:3]3[CH2:2]1

Participants

7

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 128585822a,3,4,5-Tetrahydro-1(2H)-acenaphthylenone

Product 1

HCID 866416292a,3,4,5-tetrahydro-2H-acenaphthylen-1-one oximeYield 101.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

To a mixture of 2a,3,4,5-tetrahydro-2H-acenaphthylen-1-one (12.2 g, 70.9 mmol), hydroxylamine hydrochloride (7.85 g) and water (90 ml) were slowly added sodium acetate (14.5 g), methanol (120 ml), THF (30 ml) and water (60 ml) with stirring while heating at 75° C., and the mixture was stirred for 2 hr and 40 min. After cooling to room temperature, methanol was evaporated under reduced pressure, and the obtained precipitate was collected by filtration, and washed with water to give 2a,3,4,5-tetrahydro-2H-acenaphthylen-1-one oxime (13.5 g).

Workup

  1. stirringthe mixture was stirred for 2 hr and 40 min
  2. temperatureAfter cooling to room temperature
  3. custommethanol was evaporated under reduced pressure
  4. filtrationthe obtained precipitate was collected by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-d9f0fe0bf1ed4ea2863ec399767284be
Source dataset
uspto-grants-2014_11
Patent number
US08877779B2

Reaction notes

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