Cesium carbonate → 1-(3-chloro-4-pyridinyl)-1H-pyrrole-2-carbaldehyde

HRID 251995Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 251995
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[O:7].[Cl:8][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][C:14]=1Cl.C(=O)([O-])[O-].[Cs+].[Cs+].CN1CCCC1=O>O>[Cl:8][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][C:14]=1[N:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[O:7]

Komponenten

6

Edukt 4

HCID 10796Cesium carbonateHCID 13387N-methyl-2-pyrrolidoneHCID 13854Pyrrole-2-carboxaldehydeHCID 27360813,4-Dichloropyridine

Produkt 1

HCID 866325591-(3-chloro-4-pyridinyl)-1H-pyrrole-2-carbaldehydeAusbeute 70,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of 2.0 g of 2-pyrrole carbaldehyde, 3.0 g of 3,4-dichloropyridine, 8.0 g of cesium carbonate and 30 ml of N-methylpyrrolidone was stirred at 120° C. for 25 hours. The reaction mixture was allowed to cool room temperature, and water was poured into the mixture. The mixture was extracted with ethyl acetate two times. The organic layers were combined, washed successively with water and an aqueous saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel chromatography to obtain 2.95 g of 1-(3-chloro-4-pyridinyl)-1H-pyrrole-2-carbaldehyde of the formula:

Aufarbeitung

  1. temperatureto cool room temperature
  2. extractionThe mixture was extracted with ethyl acetate two times
  3. washwashed successively with water
  4. dry with materialan aqueous saturated sodium chloride solution, dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-6474c146e2d046659865f11027c71aba
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07867949B2

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