5-(Trifluoromethyl)pyridine-2-carbonitrile → [5-(Trifluoromethyl)pyridin-2-yl]methanamine

HRID 1181383

Reaktionsgleichung

Reaktionsgleichung von HRID 1181383
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][N:4]=1)#[N:2]>C(O)C.[OH-].[NH4+].[Ni]>[NH2:2][CH2:1][C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:10])[F:11])=[CH:5][N:4]=1

Komponenten

5

Edukt 1

HCID 15353725-(Trifluoromethyl)pyridine-2-carbonitrile

Produkt 1

HCID 3796375[5-(Trifluoromethyl)pyridin-2-yl]methanamineAusbeute 30,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 935NickelKatalysatorHCID 702EthanolLösungsmittelHCID 14923Ammonium HydroxideLösungsmittel

Versuchsvorschrift

To a nitrogen flushed solution of 2-cyano-5-(trifluoromethyl)pyridine (Description 1; 8.0 g, 46.5 mmol) in a mixture of ethanol (100 ml) and ammonium hydroxide (25 ml) was added a spatula end of Raney Nickel and the resulting mixture hydrogenated at 50 psi overnight. The catalyst was removed by filtration and the filtrate was evaporated to dryness. The residue was purified by column chromatography on silica eluting with a gradient rising from 2% MeOH in dichloromethane+0.5% NH4OH to 5% MeOH in dichloromethane+0.5% NH4OH to give the title compound (2.5 g, 30%) as a yellow oil.

Aufarbeitung

  1. customhydrogenated at 50 psi overnight
  2. customThe catalyst was removed by filtration
  3. customthe filtrate was evaporated to dryness
  4. customThe residue was purified by column chromatography on silica eluting with a gradient

Quellen und Nachweise

ORD-Eintrag
ord-8b793d41cda548b9a29289ee00b56bb1
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07285563B2

Verknüpfte Notizen

Wird geladen…