Hydroxyamine hydrochloride → HCID 59925101, compound

HRID 870272Notes

Reaction equation

HRID 870272 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9](=O)[C:10]2([CH3:14])[CH3:13])=[CH:5][CH:4]=1.Cl.[NH2:17][OH:18].C([O-])(=O)C.[Na+]>CO.O>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9](=[N:17][OH:18])[C:10]2([CH3:14])[CH3:13])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 130110077-Methoxy-1,1-dimethyl-3,4-dihydronaphthalen-2(1H)-one

Product 1

HCID 59925101HCID 59925101, compoundYield 68.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 7-methoxy-1,1-dimethyl-3,4-dihydro-1H-napthalen-2-one (25.4 g, 98 mmol) in methanol (175 mL) was added a solution of hydroxylamine hydrochloride (20.5 g, 295 mmol) and sodium acetate (24.2 g, 295 mmol) in water (175 mL) and the reaction mixture was heated at 70° C. for 3 h, and cooled in ice over 30 min. The solid was collected on a Buchner funnel, stirred with methanol (125 mL) at 50° C. for 30 min, and then stirred at RT overnight. The reaction mixture was cooled to 0° C.; solid was collected on a Buchner funnel, rinsed with cold methanol (20 mL) and dried under vacuum to give the title compound (14.7 g).

Workup

  1. temperaturecooled in ice over 30 min
  2. customThe solid was collected on a Buchner funnel
  3. stirringstirred at RT overnight
  4. temperatureThe reaction mixture was cooled to 0° C.
  5. customsolid was collected on a Buchner funnel
  6. washrinsed with cold methanol (20 mL)
  7. customdried under vacuum

Sources & evidence

ORD record
ord-0d6c82706a60458386e889dcc1b99975
Source dataset
uspto-grants-2015_03
Patent number
US08969370B2

Reaction notes

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