Hydroxyamine hydrochloride → HCID 87294738, compound

HRID 1506449Notes

Reaction equation

HRID 1506449 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[CH3:13])[C:9](=O)[CH2:8][CH2:7][CH2:6]2.Cl.[NH2:16][OH:17].C([O-])(=O)C.[Na+]>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[CH3:13])/[C:9](=[N:16]/[OH:17])/[CH2:8][CH2:7][CH2:6]2

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 113559636-methoxy-7-methyl-3,4-dihydronaphthalen-1(2H)-one

Product 1

HCID 87294738HCID 87294738, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To 6-methoxy-7-methyl-3,4-dihydronaphthalen-1(2H)-one (0.500 g, 2.63 mmol) in methanol (10 mL) were sequentially added hydroxylamine hydrochloride (0.292 g, 4.21 mmol) and sodium acetate (0.345 g, 4.21 mmol) at room temperature. The reaction mixture was heated at 60° C. for 2 h. The reaction mixture was concentrated under vacuum. The residue was dissolved in 25 mL ethyl acetate, transferred to a separating funnel and washed with water (2×10 mL). The ethyl acetate layer was dried over sodium sulfate and concentrated to give (E)-6-methoxy-7-methyl-3,4-dihydronaphthalen-1(2H)-one oxime as viscous orange-colored liquid (0.498 g, 2.43 mmol, 92%). The product had an HPLC ret. time=3.10 min (condition B). LC/MS M+1=206.0.

Workup

  1. customat room temperature
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. dissolutionThe residue was dissolved in 25 mL ethyl acetate
  4. customtransferred to a separating funnel
  5. washwashed with water (2×10 mL)
  6. dry with materialThe ethyl acetate layer was dried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8fb235753eae4bc9ad218c77d6e9a895
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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