Potassium Iodide → (2-Acetyl-phenylamino)-phenyl-acetic acid ethyl ester

HRID 76995

Reaktionsgleichung

Reaktionsgleichung von HRID 76995
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:10])[CH3:9].Br[CH:12]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:13]([O:15][CH2:16][CH3:17])=[O:14].CCN(C(C)C)C(C)C.[I-].[K+]>C(#N)C>[CH2:16]([O:15][C:13](=[O:14])[CH:12]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:10])[CH3:9])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH3:17]

Komponenten

6

Edukt 4

HCID 4875Potassium IodideHCID 110862'-AminoacetophenoneHCID 81531DiisopropylethylamineHCID 97780Ethyl bromophenylacetate

Produkt 1

HCID 59401176(2-Acetyl-phenylamino)-phenyl-acetic acid ethyl esterAusbeute 100,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

1-(2-Aminophenyl)ethanone (250 mg, 1.85 mmol), ethyl 2-bromo-2-phenylacetate (0.22 ml, 1.23 mmol), DIPEA (0.32 mL, 1.85 mmol) and a catalytic amount of potassium iodide are dissolved in acetonitrile (4 mL) and heated under MW irradiation at 100° C. for 2 hours and then at 120° C. for 1 hour. Acetonitrile is evaporated and the crude is purified by flash chromatography (petroleum ether/EtOAc=93/7) to obtain intermediate I110 as a yellow oil (367 mg, quantitative yield).

Aufarbeitung

  1. customAcetonitrile is evaporated
  2. customthe crude is purified by flash chromatography (petroleum ether/EtOAc=93/7)

Quellen und Nachweise

ORD-Eintrag
ord-5b91be84d1ed4518a37485df7db91f75
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835682B2

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