O-methylhydroxylammonium chloride → HCID 6514828, compound

HRID 1497029Notes

Reaction equation

HRID 1497029 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH2:7][C:8]2=O.C[O:15][NH3+:16].[Cl-].C([O-])(=O)C.[Na+]>CO>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH2:7]/[C:8]/2=[N:16]/[OH:15]

Participants

5

Reactant 3

HCID 11639O-methylhydroxylammonium chlorideHCID 366205-MethoxytetraloneHCID 517045Sodium Acetate

Product 1

HCID 6514828HCID 6514828, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 5-methoxy-3,4-dihydronaphthalen-1(2H)-one (200 mg, 1.14 mmol) and hydroxylamine methyl ether hydrochloride (284 mg, 3.40 mmol) in MeOH (5 mL) was added sodium acetate (279 mg, 3.40 mmol). The reaction mixture was heated at 60° C. for 1 h, cooled and partitioned between H2O and EtOAc. The organic layer was separated, dried over Na2SO4, filtered, and concentrated in vacuo to give Intermediate 34A (0.20 g, 1.1 mmol, 92% yield) which was used directly in the next step without further purification. LCMS=1.78 min [M+1]=192.1 (Method B).

Workup

  1. temperaturecooled
  2. custompartitioned between H2O and EtOAc
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-931f9b4e5d9649ff95b7d4871f73e3df
Source dataset
uspto-grants-2015_12
Patent number
US09199946B2

Reaction notes

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