Methylhydroxylamine → HCID 67954883, compound

HRID 1619180Notes

Reaction equation

HRID 1619180 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)/[CH:25]=[CH:26]/[N:27]([CH3:29])C)=[CH:19][C:18]=1[CH3:31])/[C:5]([O:7][CH3:8])=[O:6].C[NH:33]O>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]2[CH:25]=[CH:26][N:27]([CH3:29])[N:33]=2)=[CH:19][C:18]=1[CH3:31])/[C:5]([O:7][CH3:8])=[O:6]

Participants

4

Reactant 2

HCID 11647MethylhydroxylamineHCID 67955221HCID 67955221, compound

Product 1

HCID 67954883HCID 67954883, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(E)-methyl 3-methoxy-2-(2-((4-((E)-3-(dimethylamino)acryloyl)-2,5-dimethylphenoxy)-methyl)phenyl)acrylate (0.11 g, 0.25 mmol) obtained in Step 1 was reacted with 17 mg (1.5 eq) of methylhydroxyamine in 10 mL of methanol at room temperature for 3 hours with stirring, and then the reaction solvent was removed at a reduced pressure. The residue was stirred in water (20 mL), and the aqueous layer was extracted twice with 30 mL of dichloromethane. The organic layer was dried over anhydrous magnesium sulfate and concentrated in a vacuum. Purification by chromatography afforded (E)-methyl 3-methoxy-2-(2-((2,5-dimethyl-4-(1-methyl-1H-pyrazol-3-yl)phenoxy)methyl)phenyl)acrylate as a white solid (75 mg, yield: 74%).

Workup

  1. customthe reaction solvent was removed at a reduced pressure
  2. stirringThe residue was stirred in water (20 mL)
  3. extractionthe aqueous layer was extracted twice with 30 mL of dichloromethane
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated in a vacuum
  6. customPurification by chromatography

Sources & evidence

ORD record
ord-93020a038e994cd7b5aa8e42c912d3a2
Source dataset
uspto-grants-2014_07
Patent number
US08772290B2

Reaction notes

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