2-Toluidine hydrochloride → 2-[(2-Methylphenyl)amino]-2-oxoacetyl chloride

HRID 1953837Notes

Reaction equation

HRID 1953837 reaction equation
[C:1]([Cl:6])(=[O:5])[C:2](Cl)=[O:3].Cl.[NH2:8][C:9]1[C:10]([CH3:15])=[CH:11][CH:12]=[CH:13][CH:14]=1>O1CCCC1>[Cl:6][C:1](=[O:5])[C:2]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:15])=[O:3]

Participants

4

Reactant 2

HCID 124842-Toluidine hydrochlorideHCID 65578Oxalyl chloride

Product 1

HCID 232982202-[(2-Methylphenyl)amino]-2-oxoacetyl chloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Oxalyl chloride (5.8 g, 46 mmol) in tetrahydrofuran (2 mL) was heated to reflux and o-toluidine hydrochloride was added portionwise over ten minutes. After addition, the reaction mixture was refluxed for four hours and concentrated in vacuo to yield 1-Chloro-2-[(2-methylphenyl)amino]ethandione. This intermediate was dissolved in chloroform (4 mL) and aluminum chloride (2.6 g) was added portionwise. The reaction mixture was heated at reflux overnight, and chromatographed through Merck silica gel (100 g) using (9:1:0.1) toluene:acetone:acetic acid solvent system. The appropriate fractions were combined and concentrated to yield the title compound (90 mg, 5.6%).

Workup

  1. temperatureto reflux
  2. additionAfter addition
  3. temperaturethe reaction mixture was refluxed for four hours
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d651aa99399746f5a6021e08e8d53146
Source dataset
uspto-grants-2000_09
Patent number
US06117885

Reaction notes

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