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

HRID 2104409ノート

反応式

HRID 2104409 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-344dad770ea44432896190fb46a54b74
出典データセット
uspto-grants-2009_08
特許番号
US07576135B2

反応ノート

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