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

HRID 1392777Notes

Reaction equation

HRID 1392777 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-hydroxy-benzotriazole (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-ce9ff703537848ad8cede2806c3a9804
Source dataset
uspto-grants-2008_03
Patent number
US07342014B2

Reaction notes

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