O-Methylhydroxylamine hydrochloride → HCID 88531355, compound

HRID 1619179Notes

Reaction equation

HRID 1619179 reaction equation
[CH3:1][O:2]/[CH:3]=[C:4](\[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][O:16][C:17]1[CH:22]=[C:21]([CH3:23])[C:20]([C:24](=O)[CH2:25][O:26][CH3:27])=[CH:19][C:18]=1[CH3:29])/[C:5]([O:7][CH3:8])=[O:6].Cl.[CH3:31][O:32][NH2:33]>CO>[CH3:1][O:2]/[CH:3]=[C:4](\[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][O:16][C:17]1[CH:22]=[C:21]([CH3:23])[C:20](/[C:24](=[N:33]/[O:32][CH3:31])/[CH2:25][O:26][CH3:27])=[CH:19][C:18]=1[CH3:29])/[C:5]([O:7][CH3:8])=[O:6]

Participants

4

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 67955390HCID 67955390, compound

Product 1

HCID 88531355HCID 88531355, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 30 mL of methanol, 0.2 g (0.50 mmol) of (E)-methyl 3-methoxy-2-(2-((4-(2-methoxyacetyl)-2,5-dimethylphenoxy)methyl)phenyl)acrylate obtained in Step 2 was reacted with 0.21 g (5 eq) of methoxyamine hydrochloride at room temperature for 15 hours with stirring. After completion of the reaction, the solvent was removed in a vacuum, and the residue was stirred in water (30 mL) and extracted twice with 30 mL of dichloromethane. The organic layer was dried over anhydrous magnesium sulfate and concentrated in a vacuum. Purification by silica gel chromatography afforded 0.1 g of (E)-methyl 3-methoxy-2-(2-((4-((Z)-2-methoxy-1-(methoxyimino)ethyl)2,5-dimethylphenoxy)methyl)phenyl)acrylate as a white solid (yield: 50%).

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was removed in a vacuum
  3. stirringthe residue was stirred in water (30 mL)
  4. extractionextracted twice with 30 mL of dichloromethane
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated in a vacuum
  7. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-95f458a2e3bf4d6d90233c811658c1a3
Source dataset
uspto-grants-2014_07
Patent number
US08772290B2

Reaction notes

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