ChemicalBook CAS DataBase List 4-Chloro-3-cyanopyridine

4-Chloro-3-cyanopyridine synthesis

8synthesis methods

Product Name:4-Chloro-3-cyanopyridine
CAS Number:89284-61-7
Molecular formula:C6H3ClN2
Molecular Weight:138.55

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Yield:89284-61-7 87.89%

Reaction Conditions:

with triethylamine;trichlorophosphate in tetrahydrofuran at 0 - 20; for 3 h;

Steps:

24.B
Step B: Preparation of 4-chloronicotinonitrile: 4-chloronicotinamide (2.7 g, 17.24 mmol) was suspended in cold (0° C.) THF (100 mL) and triethylamine (19.23 mL, 138.0 mmol). To this was slowly added phosphoryl trichloride (1.607 mL, 17.24 mmol). The reaction mixture was allowed to stir for 3 hours while warming to room temperature. Silica gel was added and the reaction mixture was concentrated (keeping the bath temperature ˜35° C.). The residue was dry loaded onto a Biotage 40M column and eluted with CH₂Cl₂(100%) to give 2.1 g (87.89% yield) of the desired product.

References:

Miknis, Greg;Lyssikatos, Joseph P.;Laird, Ellen;Tarlton, Eugene;Buckmelter, Alexandre J.;Ren, Li;Rast, Bryson;Schlacter, Stephen T.;Wenglowsky, Steven Mark US2007/49603, 2007, A1 Location in patent:Page/Page column 47

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