Monomethylamine methanol → HCID 88229995, compound

HRID 427997Notes

Reaction equation

HRID 427997 reaction equation
[CH3:1][O:2][CH:3]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14]/[N:15]=[C:16](\[CH3:24])/[C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)[C:4](OC)=[O:5].[CH3:25][NH2:26].CO>>[CH3:1][O:2][CH:3]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14]/[N:15]=[C:16](\[CH3:24])/[C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)[C:4]([NH:26][CH3:25])=[O:5]

Participants

3

Reactant 2

HCID 57454252Monomethylamine methanolHCID 140425512HCID 140425512, compound

Product 1

HCID 88229995HCID 88229995, compoundYield 86%

Procedure

A solution of methyl (E)-α-methoxy-2-(α-methyl-4-chlorobenzylideneaminooxy)phenylacetate (0.48 g, 1.3 mmol) and 40% monomethylamine-methanol solution (10 ml) was stirred in a sealed tube at 80° C. for 15 hours. The mixture was cooled to room temperature, and then the solvent was evaporated under reduced pressure. Water was added, the mixture was adjusted to pH 1 with 1N hydrochloric acid, extracted with methylene chloride and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=3/2) to give the desired compound (E)-α-methoxy-N-methyl-2-(α-methyl-4-chlorobenzylideneaminooxy)phenylacetamide (0.41 g, 86%) as an oil.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. additionWater was added
  3. extractionextracted with methylene chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=3/2)

Sources & evidence

ORD record
ord-7136055a9c0649519304bd4e659867f1
Source dataset
uspto-grants-2001_11
Patent number
US06313150B1

Reaction notes

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