4-Chloroaniline → Ethyl 3-[(4-chlorophenyl)amino]-3-oxopropanoate

HRID 2104409Notes

Reaction equation

HRID 2104409 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[C:9]([O:15][CH2:16][CH3:17])(=[O:14])[CH2:10][C:11]([O-])=[O:12].[K+].ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O.C(OCC)(=O)C>[CH2:16]([O:15][C:9](=[O:14])[CH2:10][C:11]([NH:6][C:5]1[CH:7]=[CH:8][C:2]([Cl:1])=[CH:3][CH:4]=1)=[O:12])[CH3:17]

Participants

7

Reactant 4

HCID 78124-ChloroanilineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 3446434Potassium ethyl malonate

Product 1

HCID 1518288Ethyl 3-[(4-chlorophenyl)amino]-3-oxopropanoateYield 105.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-chloroaniline (2.0 g) in N,N-dimethylformamide (20 mL) were sequentially added at room temperature potassium ethyl malonate (3.2 g), 1-hydroxybenzotriazole (2.1 g), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (4.5 g), followed by stirring at room temperature for 2 hours. The reaction mixture was diluted with ethyl acetate and washed with saturated aqueous sodium hydrogencarbonate, 10% aqueous citric acid, and saturated brine. The organic layer was dried over sodium sulfate anhydrate, and the solvent was distilled away under reduced pressure, to thereby give the title compound (4.0 g).

Workup

  1. washwashed with saturated aqueous sodium hydrogencarbonate, 10% aqueous citric acid, and saturated brine
  2. dry with materialThe organic layer was dried over sodium sulfate anhydrate
  3. distillationthe solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-344dad770ea44432896190fb46a54b74
Source dataset
uspto-grants-2009_08
Patent number
US07576135B2

Reaction notes

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