Potassium Carbonate → HCID 22727951, Verbindung

HRID 2086070Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2086070
[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5](Cl)=[N:6][CH:7]=1.[NH2:12][C:13]1[CH:14]=[C:15]([N:19]2[CH2:23][CH2:22][CH2:21][C:20]2=[O:24])[CH:16]=[CH:17][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>ClCCCl.ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5]([NH:12][C:13]2[CH:14]=[C:15]([N:19]3[CH2:23][CH2:22][CH2:21][C:20]3=[O:24])[CH:16]=[CH:17][CH:18]=2)=[N:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 6839561-(3-Aminophenyl)pyrrolidin-2-oneHCID 70194125-Bromo-2-chloro-3-nitropyridine

Produkt 1

HCID 22727951HCID 22727951, VerbindungAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A suspension of 5-bromo-2-chloro-3-nitropyridine (3.79 g, 16 mmol), 1-(3-aminophenyl)pyrrolidin-2-one (2.56 g, 15 mmol) and potassium carbonate (2.0 g, 15 mmol) in 1,2-dichloroethane (25 ml) was heated at reflux for 60 hours. The reaction was cooled, diluted with dichloromethane (200 ml) and extracted with water. The organic phase was then dried over anhydrous sodium sulphate, filtered and pre-adsorbed on to silica (25 g). Purification by column chromatography eluting with isohexane on a gradient of ethyl acetate (10%-40%) gave 1-[3-(5-bromo-3-nitropyridin-2-ylamino)phenyl]pyrrolidin-2-one as a red solid (3.7 g, 68%).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 60 hours
  3. temperatureThe reaction was cooled
  4. extractionextracted with water
  5. dry with materialThe organic phase was then dried over anhydrous sodium sulphate
  6. filtrationfiltered and pre-adsorbed on to silica (25 g)
  7. customPurification by column chromatography
  8. washeluting with isohexane on a gradient of ethyl acetate (10%-40%)

Quellen und Nachweise

ORD-Eintrag
ord-802ee8b24a2c4f088055f85035af65ec
Quelldatensatz
uspto-grants-2004_04
Patentnummer
US06723735B1

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