Hydroxyamine hydrochloride → HCID 87294575, compound

HRID 1506310Notes

Reaction equation

HRID 1506310 reaction equation
[CH3:1][C:2]1([CH3:15])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH:12]=[CH2:13])[CH:10]=2)[C:5](=O)[CH2:4][CH2:3]1.Cl.[NH2:17][OH:18].C([O-])(=O)C.[Na+]>CO>[CH3:1][C:2]1([CH3:15])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH:12]=[CH2:13])[CH:10]=2)/[C:5](=[N:17]/[OH:18])/[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 67168875HCID 67168875, compound

Product 1

HCID 87294575HCID 87294575, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 4,4-dimethyl-6-vinyl-3,4-dihydronaphthalen-1(2H)-one (Preparation 1C, 0.201 g, 1.004 mmol) and hydroxylamine hydrochloride (0.084 g, 1.20 mmol) in methanol (3 mL) at room temperature was added sodium acetate (0.099 g, 1.20 mmol). The heterogeneous reaction mixture was heated at reflux for 1.5 h. The heterogeneous mixture was concentrated, and the solid residue was diluted with dichloromethane, washed with water, and dried over anhydrous sodium sulfate. Concentration under reduced pressure afforded (E)-4,4-dimethyl-6-vinyl-3,4-dihydronaphthalen-1(2H)-one oxime (0.210 g, 0.975 mmol, 97% yield) as a pale yellow solid. The product had an HPLC ret. time=2.64 min. (condition A); LC/MS M+1=216.0.

Workup

  1. temperatureThe heterogeneous reaction mixture was heated
  2. temperatureat reflux for 1.5 h
  3. concentrationThe heterogeneous mixture was concentrated
  4. additionthe solid residue was diluted with dichloromethane
  5. washwashed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-c7c034fc02ae44d3b2902229626f9aaf
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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