4-Chloroaniline → Ethyl N-(4-chlorophenyl)-2-oxoglycinate

HRID 1392755Notes

Reaction equation

HRID 1392755 reaction equation
C(N(CC)CC)C.Cl[C:9](=[O:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11].[Cl:16][C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=1.C(=O)([O-])O.[Na+]>C(Cl)Cl>[Cl:16][C:17]1[CH:23]=[CH:22][C:20]([NH:21][C:9](=[O:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 78124-ChloroanilineHCID 8471TriethylamineHCID 20884Ethoxalyl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 79380Ethyl N-(4-chlorophenyl)-2-oxoglycinate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (1.52 ml) and ethyl chlorooxoacetate (1.11 ml) were successively added to a solution of 4-chloroaniline (1.16 g) in methylene chloride (26 ml), and the mixture was stirred at room temperature for 14 hours. After a saturated aqueous solution of sodium hydrogencarbonate was added to the reaction mixture to conduct liquid separation, the resultant organic layer was successively washed with a 10% aqueous solution of citric acid and saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. After the solvent was concentrated under reduced pressure, hexane was added to the residue to deposit crystals, and the crystals were collected by filtration and dried to obtain the title compound (1.89 g).

Workup

  1. customliquid separation
  2. washthe resultant organic layer was successively washed with a 10% aqueous solution of citric acid and saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationAfter the solvent was concentrated under reduced pressure, hexane
  5. additionwas added to the residue to deposit crystals
  6. filtrationthe crystals were collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-ca39890d42df4debaa3da04cf2d7f8ec
Source dataset
uspto-grants-2008_03
Patent number
US07342014B2

Reaction notes

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