Methylamine → (E)-2-(2-Hydroxymethylphenyl)-2-methoxyimino-N-methyl-acetamide

HRID 1492039Notes

Reaction equation

HRID 1492039 reaction equation
C[O:2][C:3](=O)[C:4]([C:8]1C=[CH:12][CH:11]=[CH:10][C:9]=1CBr)=[N:5][O:6][CH3:7].[C:17]([O-:20])(=O)[CH3:18].[K+].[CH3:22][NH2:23]>C1COCC1.O>[CH3:22][NH:23][C:3](=[O:2])/[C:4](/[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:18]=1[CH2:17][OH:20])=[N:5]/[O:6][CH3:7]

Participants

6

Reactant 3

HCID 6329MethylamineHCID 517044Potassium AcetateHCID 54028047Methyl 2-[2-(bromomethyl)phenyl]-2-(methoxyimino)acetate

Product 1

HCID 15376320(E)-2-(2-Hydroxymethylphenyl)-2-methoxyimino-N-methyl-acetamideYield 67.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl-2-(2-bromomethylphenyl)-2-methoxyiminoacetate (2.00 g) and potassium acetate (1.37 g) were suspended in THF, and the suspension was heated under reflux for 3 hours. The reaction mixture was cooled to room temperature, and 30% methanolic methylamine (5.4 g) was added thereto. The resultant mixture was stirred for 10 hours, diluted with water and neutralized, followed by extraction with ethyl acetate. The solvent was dried and distilled off, and the residue was purified by silica gel column chromatography, whereby there was obtained (E)-N-methyl-2-(2-hydroxymethylphenyl)-2-methoxyiminoacetamide (1.05 g).

Workup

  1. temperaturethe suspension was heated
  2. temperatureunder reflux for 3 hours
  3. extractionneutralized, followed by extraction with ethyl acetate
  4. customThe solvent was dried
  5. distillationdistilled off
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b755ffefbe114a3f94c7d563063bd4f8
Source dataset
uspto-grants-1994_12
Patent number
US05371223

Reaction notes

Loading…