2-CHLORO-6-(TRIFLUOROMETHYL)NICOTINONITRILE

Step 3: In a preheated mixture of No.36   2-hydroxy-6-(trifluoromethyl)nicotinonitrile (45 g, 0.24 mol) and No.38   phosphorous oxychloride (90 mL), No.39   phosphorous pentachloride (74.6 g, 0.359 mol) was added in a small portion. A vigorous frothing came during initial addition. After complete addition the mixture was refluxed gently for 22 h. It was then checked TLC after quenching a small amount of reaction mass with saturated sodium bicarbonate solution which showed complete conversion of starting material to the product. The whole reaction mixture was then allowed to cool to 50-55° C. and excess phosphoryl chloride was removed under reduced pressure. The residue was then poured into crushed ice (−100 g) and neutralized with saturated sodium bicarbonate solution. The aqueous part was then extracted with ethyl acetate (3×200 mL). The whole organic layer was then washed with water (200 mL) and brine (200 mL) and dried over anhydrous magnesium sulfate. The removal of organic solvent under reduced pressure afforded a brown liquid compound, which was purified by column chromatography (eluent: 10percent ethyl acetate in No.40   n-hexane) to afford No.41   2-chloro-6-(trifluoromethyl)nicotinonitrile (36 g, 73percent) as a light brown liquid.Step 3: In a preheated mixture of 2-hydroxy-6-(trifluoromethyl)nicotinonitrile (45 g, 0.24 mol) and phosphorous oxychloride (90 mL), phosphorous pentachloride (74.6 g, 0.359 mol) was added in a small portion. A vigorous frothing came during initial addition. After complete addition the mixture was refluxed gently for 22 h. It was then checked TLC after quenching a small amount of reaction mass with saturated sodium bicarbonate solution which showed complete conversion of starting material to the product. The whole reaction mixture was then allowed to cool to 50-55 °C and excess phosphoryl chloride was removed under reduced pressure. The residue was then poured into crushed ice (-100 g) and neutralized with saturated sodium bicarbonate solution. The aqueous part was then extracted with ethyl acetate (3 x 200 mL). The whole organic layer was then washed with water (200 mL) and brine (200 mL) and dried over anhydrous magnesium sulfate. The removal of organic solvent under reduced pressure afforded a brown liquid compound, which was purified by column chromatography ( eluent: 10percent ethyl acetate in n-hexane) to afford 2-chloro-6- (trifluoromethyl)nicotinonitrile (36 g, 73 percent) as a light brown liquid.

Molecular Weight:206.55
XLogP3:2.5
Hydrogen Bond Acceptor Count:5
Exact Mass:205.9858603
Monoisotopic Mass:205.9858603
Topological Polar Surface Area:36.7
Heavy Atom Count:13
Complexity:232
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes