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

HRID 902883Notes

Reaction equation

HRID 902883 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([O-:5])=O.[K+].ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[Cl:33][C:34]1[CH:40]=[CH:39][C:37]([NH2:38])=[CH:36][CH:35]=1>CN(C)C=O.C(OCC)(=O)C>[Cl:33][C:34]1[CH:40]=[CH:39][C:37]([NH:38][C:3](=[O:5])[CH2:2][C:1]([O:7][CH2:8][CH3:9])=[O:6])=[CH:36][CH:35]=1

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

Potassium ethyl malonate (3.2 g), 1-hydroxybenzotriazole (2.1 g) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (4.5 g) were successively added to a solution of 4-chloroaniline (2.0 g) in N,N-dimethylformamide (20 ml) at room temperature, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted with ethyl acetate and washed with a saturated aqueous solution of sodium hydrogencarbonate, a 10% aqueous solution of citric acid and saturated aqueous solution of sodium chloride. After the resultant organic layer was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure to obtain the title compound (4.0 g).

Workup

  1. washwashed with a saturated aqueous solution of sodium hydrogencarbonate
  2. dry with materialAfter the resultant organic layer was dried over anhydrous sodium sulfate
  3. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-addc4511a7dd44a9b791fdafe16a50d6
Source dataset
uspto-grants-2008_04
Patent number
US07365205B2

Reaction notes

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