Methylamine → HCID 88229995, compound

HRID 617395Notes

Reaction equation

HRID 617395 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

4

Reactant 2

HCID 6329MethylamineHCID 140425512HCID 140425512, compound

Product 1

HCID 88229995HCID 88229995, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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-dff51657835c404590a9e18efc61e16a
Source dataset
uspto-grants-1999_09
Patent number
US05948819

Reaction notes

Loading…