Potassium Carbonate → 1-(3-Methoxy-4-((6-methoxypyridin-3-yl)methoxy)phenyl)ethan-1-one oxime

HRID 2178389Notes

Reaction equation

HRID 2178389 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:19](=O)[CH3:20])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]1[CH:12]=[N:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].S(O)(O)(=O)=O.[NH2:33][OH:34]>CO.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:19](=[N:33][OH:34])[CH3:20])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]1[CH:12]=[N:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 159255Hydroxylamine, sulfate (1:1)HCID 1181140911-(3-Methoxy-4-((6-methoxypyridin-3-yl)methoxy)phenyl)ethan-1-one

Product 1

HCID 1317330211-(3-Methoxy-4-((6-methoxypyridin-3-yl)methoxy)phenyl)ethan-1-one oximeYield 96.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a stirred suspension of 1-(3-methoxy-4-((6-methoxypyridin-3-yl)methoxy)phenyl)ethan-1-one (5.48 g, 19.07 mmol) and potassium carbonate (10.54 g, 76.29 mmol) in methanol (100 mL) and water (10 mL) was added hydroxylamine sulfate (4.70 g, 28.61 mmol). The resulting mixture was heated to reflux. After 64 h, the mixture was allowed to cool to room temperature and was diluted with water (250 mL). The resulting suspension was filtered, and the filtercake was washed with water (50 mL) and dried to provide 5.55 g (96%) of 1-(3-methoxy-4-((6-methoxypyridin-3-yl)methoxy)phenyl)ethan-1-one oxime as a white solid.

Workup

  1. temperatureThe resulting mixture was heated to reflux
  2. filtrationThe resulting suspension was filtered
  3. washthe filtercake was washed with water (50 mL)
  4. customdried

Sources & evidence

ORD record
ord-43933bfbc4e74de08eae3fc7dbf6a889
Source dataset
uspto-grants-2015_06
Patent number
US09067914B1

Reaction notes

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