Hydrochloric Acid → 2-(2-hydroxymethylphenyl)-2-methoxyimino-N-methylacetamide

HRID 342186Notes

Reaction equation

HRID 342186 reaction equation
Cl.[CH3:2][O:3][NH2:4].C[O-].[Na+].CO.C(OC([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23](=O)[C:24]([NH:26][CH3:27])=[O:25])C)C.Cl.C(=O)(O)[O-].[Na+]>CO.O>[OH:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23](=[N:4][O:3][CH3:2])[C:24]([NH:26][CH3:27])=[O:25]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 154837862-[2-{(1-ethoxyethyl)oxymethyl}phenyl)-N-methyl-2-oxoacetamideHCID 23694274Sodium methanolate methanol

Product 1

HCID 544725602-(2-hydroxymethylphenyl)-2-methoxyimino-N-methylacetamideYield 97.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

Methoxyamine hydrochloride (7.52 g, 0.09 mol) was dissolved in methanol (60 ml), and a 28% sodium methoxide-methanol solution (19.68 g, 0.102 mol) was added to the solution under ice-cooling to obtain a suspension. A solution of 2-[2-{(1-ethoxyethyl)oxymethyl}phenyl]-N-methyl-2-oxoacetamide (15.92 g, 0.06 mol) in methanol (60 ml) was added to the suspension. The mixture was stirred under reflux for 2 hours. After completion of the reaction, about half of the methanol was evaporated under reduced pressure, water (400 ml) was added, and the mixture was extracted with dichloromethane (200 ml) twice. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was dissolved in methanol (30 ml), a 36% aqueous hydrochloric acid solution (0.61 g, 0.006 mol) was added under ice-cooling, and the mixture was stirred for 0.5 hours. After completion of the reaction, water (370 ml) and saturated sodium bicarbonate (30 ml) were added, and the mixture was extracted with dichloromethane (200 ml) twice. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain crude 2-(2-hydroxymethylphenyl)-2-methoxyimino-N-methylacetamide (12.98 g, Yield: 97.3%, E/Z=96/4) as colorless crystals.

Workup

  1. temperaturecooling
  2. customto obtain a suspension
  3. temperatureunder reflux for 2 hours
  4. customAfter completion of the reaction
  5. customabout half of the methanol was evaporated under reduced pressure, water (400 ml)
  6. additionwas added
  7. extractionthe mixture was extracted with dichloromethane (200 ml) twice
  8. dry with materialThe extract was dried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. dissolutionThe resulting residue was dissolved in methanol (30 ml)
  11. temperaturecooling
  12. stirringthe mixture was stirred for 0.5 hours
  13. additionwere added
  14. extractionthe mixture was extracted with dichloromethane (200 ml) twice
  15. dry with materialThe extract was dried over anhydrous magnesium sulfate
  16. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6b83e9e047464c04a5ccc80343df131a
Source dataset
uspto-grants-1999_01
Patent number
US05856573

Reaction notes

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