HCID 15451892, compound → 2-(2-hydroxymethylphenyl)-2-methoxyimino-N-methylacetamide

HRID 1637005Notes

Reaction equation

HRID 1637005 reaction equation
C([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1/[C:12](=[N:16]\[O:17][CH3:18])/[C:13]([NH2:15])=[O:14])(=O)C.[CH3:19]N.CO>CO>[OH:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12](=[N:16][O:17][CH3:18])[C:13]([NH:15][CH3:19])=[O:14]

Participants

4

Reactant 2

HCID 15451892HCID 15451892, compoundHCID 57454252Monomethylamine methanol

Product 1

HCID 544725602-(2-hydroxymethylphenyl)-2-methoxyimino-N-methylacetamideYield 98.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of (E)-2-(2-acetoxymethylphenyl)-2-methoxyiminoacetamide (432 mg), 40% methylamine/methanol solution (5 ml) and methanol (5 ml) was stirred at 60° C. for 16 hours in a sealed tube. After the mixture was cooled by allowing it to stand, the solvent was evaporated under reduced pressure. The resulting residue was crystallized from ethyl acetate-hexane. The crystallization mother liquor was concentrated under reduced pressure and purified by column chromatography on silica gel (ethyl acetate:hexane=4:1) to obtain the title compound (379 mg, yield: 98.3%, white crystals) as a mixture of the E- and Z-isomers (E/Z≠93/7 determined by 1H-NMR analysis).

Workup

  1. temperatureAfter the mixture was cooled
  2. customthe solvent was evaporated under reduced pressure
  3. customThe resulting residue was crystallized from ethyl acetate-hexane
  4. concentrationThe crystallization mother liquor was concentrated under reduced pressure
  5. custompurified by column chromatography on silica gel (ethyl acetate:hexane=4:1)

Sources & evidence

ORD record
ord-58472be395014cad8b38e2d066e5773f
Source dataset
uspto-grants-2000_03
Patent number
US06037495

Reaction notes

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