2,5-Dichloropyridine-4-carbonitrile → N-(2,5-Dichloro-pyridin-4-ylmethyl)-acetamide
Reaktionsgleichung
[Cl:1][C:2]1[CH:3]=[N:4][C:5]([Cl:10])=[CH:6][C:7]=1[C:8]#[N:9].[CH3:11][C:12](OC(C)=O)=[O:13].CC(O)=O>O=[Pt]=O>[Cl:10][C:5]1[CH:6]=[C:7]([CH2:8][NH:9][C:12](=[O:13])[CH3:11])[C:2]([Cl:1])=[CH:3][N:4]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A mixture of 3,6-dichloro-4-cyanopyridine (prepared according to WO 9633975) (3.40 g, 19.65 mmol) and PtO2 (0.40 g) in 1:1 Ac2O/AcOH (60 mL) was shaken in a Parr hydrogenation apparatus at 30 psi H2 for 6 h. The reaction mixture was filtered through a pad a celite and the filtered solids washed with EtOAc. The combined filtrate and washings were concentrated in vacuo and the resulting white solid purified by column chromatography on a 120 g ISCO combi-flash cartridge (silica gel, 20:80 to 100:0 EtOAc/hexane) to afford N-(2,5-Dichloro-pyridin-4-ylmethyl)-acetamide (1.73 g, 40%) as a white solid.