Ammonia → Imidazo[1,5-a]pyridine-3-acetonitrile

HRID 566253Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 566253
[C:1]([CH2:3][C:4]([NH:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)=O)#[N:2].P(Cl)(Cl)(Cl)=O.N>C(Cl)(Cl)Cl>[CH:7]1[N:6]=[C:4]([CH2:3][C:1]#[N:2])[N:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=12

Komponenten

5

Edukt 3

HCID 222AmmoniaHCID 24813Phosphorus oxychlorideHCID 2799775HCID 2799775, Verbindung

Produkt 1

HCID 21265783Imidazo[1,5-a]pyridine-3-acetonitrileAusbeute 35,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

2-Cyano-N-(2-pyridylmethyl)acetamide (15.51 g) was dissolved in chloroform (80 ml). To the solution was added phosphorus oxychloride (40 ml), which was refluxed for 4 hours. The reaction mixture was added to ice-water in limited amounts, to which was added a 25% aqueous ammonia (140 ml) to neutralize, which was then shaken. The aqueous layer was subjected to extraction with ethyl acetate (150 ml) twice. The organic layers were combined and dried over anhydrous magnesium sulfate, followed by concentration. The concentrate was purified by means of a column chromatography (carrier: silica gel, 250 g, developing solvent: ethyl acetate) to afford the title compound (5.00 g).

Aufarbeitung

  1. temperaturewas refluxed for 4 hours
  2. extractionThe aqueous layer was subjected to extraction with ethyl acetate (150 ml) twice
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationfollowed by concentration
  5. customThe concentrate was purified by means of a column chromatography (carrier: silica gel, 250 g, developing solvent: ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-721a2bd50ebb4bc3a5edf42059a93a46
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06174877B1

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