5-Nitro-3-(trifluoromethyl)-2-pyridinecarbonitrile → 5-Amino-3-(trifluoromethyl)pyridine-2-carbonitrile

HRID 1257087Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1257087
[C:1]([C:3]1[C:8]([C:9]([F:12])([F:11])[F:10])=[CH:7][C:6]([N+:13]([O-])=O)=[CH:5][N:4]=1)#[N:2]>CCOC(C)=O.CC(O)=O.[Fe]>[NH2:13][C:6]1[CH:7]=[C:8]([C:9]([F:12])([F:10])[F:11])[C:3]([C:1]#[N:2])=[N:4][CH:5]=1

Komponenten

4

Edukt 1

HCID 218748935-Nitro-3-(trifluoromethyl)-2-pyridinecarbonitrile

Produkt 1

HCID 135322465-Amino-3-(trifluoromethyl)pyridine-2-carbonitrileAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 22609514Ethyl acetate acetateLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

2-cyano-5-nitro-3-trifluoromethylpyridine (7 mg, 0.032 mmol) is dissolved in 1:1 EtOAc/AcOH (1 mL) and heated to 65° C. Iron powder (9 mg, 0.161 μmol, 5 eq, 325 mesh) is added and the mixture stirred for 2 hours. The mixture is filtered through celite, and the filtrate is concentrated under vacuo. The crude residue is purified by flash chromatography on silica gel (hexane/EtOAc) to afford 4 mg (67%) of the desired product.

Aufarbeitung

  1. filtrationThe mixture is filtered through celite
  2. concentrationthe filtrate is concentrated under vacuo
  3. customThe crude residue is purified by flash chromatography on silica gel (hexane/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-51524c6e575240f690582df517a595e5
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461343B2

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