Methylamine → 2-(2-hydroxymethylphenyl)-2-methoxyimino-N-methylacetamide

HRID 2081632Notes

Reaction equation

HRID 2081632 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 544725602-(2-hydroxymethylphenyl)-2-methoxyimino-N-methylacetamideYield 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-7d683e75819d4daa91223f15acdba589
Source dataset
uspto-grants-1993_02
Patent number
US05185342

Reaction notes

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