Hydroxyamine hydrochloride → HCID 72307872, compound

HRID 449524Notes

Reaction equation

HRID 449524 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]2=O)=[CH:4][CH:3]=1.Cl.[NH2:14][OH:15].C([O-])(=O)C.[Na+]>C(O)C.O>[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]2=[N:14][OH:15])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 5718187-hydroxy-3,4-dihydro-2H-naphthalen-1-one

Product 1

HCID 72307872HCID 72307872, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

7-Hydroxy-3,4-dihydronaphthalen-1(2H)-one (0.75 g, 4.2 mmol) was dissolved in ethanol (30 mL) and water (10 mL), then the hydroxylamine hydrochloride (0.59 g, 8.5 mmol) and sodium acetate (0.70 g, 8.5 mmol) were added. The reaction was heated to 80° C. for 2 h. The reaction was allowed to cool to r.t., concentrated under reduced pressure and the residue was partitioned between ethyl acetate and 1 N HCl. The organic layer was washed with brine, dried over magnesium sulfate and concentrated under reduced pressure to give the crude product as oil. The oil was purified by flash chromatography on a silica gel column eluting hexane: ethyl acetate gradient to give 7-hydroxy-3,4-dihydronaphthalen-1(2H)-one oxime (0.70 g, 95%) as a yellow green oil. Analytical LCMS (M+H)+: m/z=178.1.

Workup

  1. temperatureto cool to r.t.
  2. concentrationconcentrated under reduced pressure
  3. customthe residue was partitioned between ethyl acetate and 1 N HCl
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto give the crude product as oil
  8. customThe oil was purified by flash chromatography on a silica gel column
  9. washeluting hexane

Sources & evidence

ORD record
ord-e7c2860de4be41d4a1b32038068aff86
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

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