Methanol → HCID 52983911, Verbindung
Reaktionsgleichung
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:10]([C:15]#N)=[N:11][CH:12]=[CH:13][CH:14]=2)[CH:6]=[CH:7][CH:8]=1.[OH-:17].[Na+].C[OH:20]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:10]([C:15]([OH:20])=[O:17])=[N:11][CH:12]=[CH:13][CH:14]=2)[CH:6]=[CH:7][CH:8]=1Komponenten
4
Versuchsvorschrift
A mixture of 3-(3-methoxyphenyl)-pyridine-2-carbonitrile (12.00 g), 15 M aqueous NaOH solution (40 mL), and methanol (60 mL) is stirred at reflux temperature for 7 h. After cooling to room temperature, most of the methanol is evaporated and the residue is cooled in an ice bath and adjusted to pH value ca. 4-5 by the careful addition of concentrated hydrochloric acid. The resulting mixture is concentrated to ca. 50 ml by evaporation and extracted with dichloromethane/methanol (9:1) several times. The aqueous phase is then adjusted to pH value 2-3 using concentrated hydrochloric acid and extracted again with dichloromethane/methanol (9:1). The combined extracts are dried (Na2SO4) and the solvent is evaporated to give the title compound as a foam-like solid. Yield: 11.88 g (91% of theory); LC (method 1): tR=1.70 min; Mass spectrum (ESI+): m/z=230 [M+H]+.