Monomethylamine methanol → HCID 86755220, compound

HRID 1637009Notes

Reaction equation

HRID 1637009 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][OH:17])[C:13]([NH2:15])=[O:14])(=O)C.[CH3:18]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][OH:17])[C:13]([NH:15][CH3:18])=[O:14]

Participants

4

Reactant 2

HCID 57454252Monomethylamine methanolHCID 73604849HCID 73604849, compound

Product 1

HCID 86755220HCID 86755220, compoundYield 67.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-(2-acetoxymethylphenyl)-2-hydroxyiminoacetamide (1.00 g, E/Z≠65/35), a 40% methylamine/methanol solution (2.1 ml) and methanol (6.3 ml) was stirred at 40° C. for 6 hours. After the mixture was cooled by allowing it to stand, the solvent was evaporated under reduced pressure to obtain the crude product (E/Z≠98/2). This crude product was purified by column chromatography on silica gel (ethyl acetate) and crystallized from ethyl acetate-hexane to obtain the title compound as crystals (594 mg, E/Z≠93/7, yield: 67.4%).

Workup

  1. temperatureAfter the mixture was cooled
  2. customthe solvent was evaporated under reduced pressure
  3. customto obtain the crude product (E/Z≠98/2)
  4. customThis crude product was purified by column chromatography on silica gel (ethyl acetate)
  5. customcrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-d7a99edfa1ee47aca56d113e52e429a2
Source dataset
uspto-grants-2000_03
Patent number
US06037495

Reaction notes

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