Hydrochloric Acid → N-methyl-2-(2-methylphenyl)-2-oxoacetamide

HRID 273928Notes

Reaction equation

HRID 273928 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:12])[C:9](Cl)=[O:10].[CH3:13][NH2:14].O.Cl>C1COCC1.CO>[CH3:13][NH:14][C:9](=[O:10])[C:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH3:1])=[O:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 6329MethylamineHCID 21470370(2-Methylphenyl)(oxo)acetyl chloride

Product 1

HCID 15239356N-methyl-2-(2-methylphenyl)-2-oxoacetamideYield 50.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The crude 2-(2-methylphenyl)glyoxyloyl chloride (0.91 g, 5 mmol) were dissolved in dry THF (10 ml), and a 40% solution (1.55 g) of methylamine (20 mmol) in methanol was added thereto, followed by stirring at room temperature for 1 hour. After completion of the reaction, water (100 ml) was added to the reaction mixture which was then adjusted to below pH 2 by addition of conc. HCl and extracted with ethyl acetate (100 ml). The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate/n-hexane) to give N-methyl-2-(2-methylphenyl)-2-oxoacetamide (0.45 g; yield, 50.8%) as a colorless oil.

Workup

  1. additionwas added to the reaction mixture which
  2. extractionextracted with ethyl acetate (100 ml)
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-e3307d9258be46b7a886004ac1d90910
Source dataset
uspto-grants-1995_02
Patent number
US05387714

Reaction notes

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