Acetic acid, 2-oxo-, methyl ester → methyl (2E)-2-[(2-chlorophenyl)hydrazinylidene]acetate

HRID 7404

Reaction equation

HRID 7404 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[CH:2]=O.Cl.[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][NH2:16]>CO>[Cl:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15]/[N:16]=[CH:2]/[C:1]([O:5][CH3:6])=[O:4]

Participants

4

Reactant 2

HCID 70205Acetic acid, 2-oxo-, methyl esterHCID 4432872-Chlorophenylhydrazine hydrochloride

Product 1

HCID 19868318methyl (2E)-2-[(2-chlorophenyl)hydrazinylidene]acetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl glyoxylate (6.8 g, 77 mmol) in methanol (150 mL) was added 2-chlorophenylhydrazine hydrochloride (12.5 g, 77 mmol) and the mixture was heated at reflux overnight, cooled and concentrated. The residue was re-dissolved in toluene and concentrated to give the title compound of Step A.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux overnight
  3. temperaturecooled
  4. concentrationconcentrated
  5. dissolutionThe residue was re-dissolved in toluene
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a1a53def4c664a96999097c0e8311779
Source dataset
uspto-grants-2006_08
Patent number
US07087598B2

Linked notes

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