Dimethylformamide → 6-Aminopicolinonitrile

HRID 2169999Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2169999
Br[C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][CH:3]=1.C(OCC)(=O)C.[CH3:15][N:16](C)C=O>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:8][C:6]1[N:7]=[C:2]([C:15]#[N:16])[CH:3]=[CH:4][CH:5]=1

Komponenten

6

Edukt 3

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 3008092-Amino-6-bromopyridine

Produkt 1

HCID 5642986-Aminopicolinonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11186Zinc cyanide (Zn(CN)2)KatalysatorHCID 178418397HCID 178418397, VerbindungKatalysator

Reaktionsbedingungen

Temperatur
170 °C

Versuchsvorschrift

340 mg (2.89 mmol, 1 eq) of zinc cyanide are added to 500 mg (2.89 mmol, 1 eq) of 6-bromopyridin-2-ylamine in 10 ml of dimethylformamide in a microwave tube. 170 mg (0.147 mmol, 0.05 eq) of tetrakis(triphenylphosphine)palladium are added. The medium is heated at 170° C. for 1 hour 30 minutes in a microwave oven. 50 ml of ethyl acetate are added to the medium, which is filtered over celite. The filtrate is washed with water and extracted with ethyl acetate. The organic phases are combined and dried over sodium sulphate. The residue is triturated in heptane. 6-Aminopyridine-2-carbonitrile is obtained in the form of an orange solid.

Aufarbeitung

  1. filtrationis filtered over celite
  2. washThe filtrate is washed with water
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over sodium sulphate
  5. customThe residue is triturated in heptane

Quellen und Nachweise

ORD-Eintrag
ord-ca3e6d5242184798b09a0a4dbc81f5ce
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09050266B2

Notizen zur Reaktion

Wird geladen…