ChemicalBook CAS DataBase List 2-Cyano-3-chloro-5-(trifluoromethyl)-pyridine

2-Cyano-3-chloro-5-(trifluoromethyl)-pyridine synthesis

11synthesis methods

Product Name:2-Cyano-3-chloro-5-(trifluoromethyl)-pyridine
CAS Number:80194-70-3
Molecular formula:C7H2ClF3N2
Molecular Weight:206.55

2-Cyano-3-chloro-5-(trifluoromethyl)-pyridine is synthesized from pyridine and chlorinated carbon compounds.

143-33-9 Synthesis

143-33-9
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2,3-Dichloro-5-(trifluoromethyl)pyridine

69045-84-7
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2-Cyano-3-chloro-5-(trifluoromethyl)-pyridine

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Yield: 75.7%

Reaction Conditions:

Stage #1:2,3-dichloro-5-trifluoromethylpyridine with dmap in propiononitrileHeating / reflux;
Stage #2:sodium cyanide in water;propiononitrile for 5 h;

Steps:

53.A
2,3-dichloro-5-(trifluoromethyl)pyridine (5.65 mL, 40.5 mmol) was combined with 4-(dimethylamino)pyridine (5.20 g, 42.6 mmol) and propionitrile (65 mL), heated to reflux and agitated overnight. The mixture was cooled to ambient temperature and solution of sodium cyanide (3.00 g, 61.2 mmol) in water (11 mL) was added. After stirring for 5 hours, the reaction was diluted with water (25 mL) and organic phase was separated, washed with water and 2M HCl, dried and evaporated to give the product, 3-chloro-5- (trifluoromethyl)picolinonitrile (6.33 g, 75.7% yield) as red liquid.

References:

ARRAY BIOPHARMA INC. WO2008/118718, 2008, A2 Location in patent:Page/Page column 76

773837-37-9 Synthesis