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

HRID 2104377Notes

Reaction equation

HRID 2104377 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[C:17](=[O:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19].C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH2:21]([O:20][C:18](=[O:19])[C:17]([NH:6][C:5]1[CH:7]=[CH:8][C:2]([Cl:1])=[CH:3][CH:4]=1)=[O:23])[CH3:22]

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

To a solution of 4-chloroaniline (1.16 g) in methylene chloride (26 mL) were sequentially added triethylamine (1.52 mL) and ethyl chlorooxoacetate (1.11 mL) under ice cooling, and the thus-obtained mixture was stirred at room temperature for 14 hours. Saturated aqueous sodium hydrogencarbonate was added to the reaction mixture to partition the mixture. The organic layer was sequentially washed with 10% aqueous citric acid and saturated brine, and was dried over sodium sulfate anhydrate. The solvent was concentrated under reduced pressure, and hexane was added to the residue. The precipitated crystals were collected by filtration, and were dried, to thereby give the title compound (1.89 g).

Workup

  1. customto partition the mixture
  2. washThe organic layer was sequentially washed with 10% aqueous citric acid and saturated brine
  3. dry with materialwas dried over sodium sulfate anhydrate
  4. concentrationThe solvent was concentrated under reduced pressure, and hexane
  5. additionwas added to the residue
  6. filtrationThe precipitated crystals were collected by filtration
  7. customwere dried

Sources & evidence

ORD record
ord-787405e7feee4934a032f149a6a9b99c
Source dataset
uspto-grants-2009_08
Patent number
US07576135B2

Reaction notes

Loading…