Reaktion #88406

Reaktionsgleichung

sodium hydroxide

Thionyl chloride

2,2,2-trifluoro-1-phenylethanone

2-aminopyridine-4-carboxylic acid methyl ester

→

title compound

Ausbeute 27.7%

(Z)-methyl 2-((2,2,2-trifluoro-1-phenylethylidene)amino)isonicotinate

Ausbeute 27.7%

Lösungsmittel

pyridine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe mixed solution was then extracted with ethyl acetate
2. 2
   Trocknenthe gathered organic layer was then dried over anhydrous sodium sulfate
3. 3
   workup.DISTILLATIONAfter that, the solvent was distilled away under reduced pressure
4. 4
   SonstigeThe obtained residue was purified by silica gel column chromatography (silica gel: eluent; heptane:ethyl acetate=2:1-1:1)

Vorschrift

Thionyl chloride (2.2 ml) was added at 0° C. to a pyridine (4.8 ml) solution of 2,2,2-trifluoro-1-phenylethanone (5.1 g) and 2-aminopyridine-4-carboxylic acid methyl ester (4.5 g). The temperature of the reaction solution was increased to room temperature, and the reaction solution was then stirred for 1 hour. Thereafter, the reaction solution was poured into a 1 N sodium hydroxide aqueous solution, and the mixed solution was then extracted with ethyl acetate. Organic layers were gathered, and the gathered organic layer was then dried over anhydrous sodium sulfate. After that, the solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel column chromatography (silica gel: eluent; heptane:ethyl acetate=2:1-1:1), so as to obtain the title compound (2.5 g) in the form of a yellow liquid.

Quelle