Hydrochloric Acid → 2-(6-Chloropyridin-3-yl)acetonitrile

Participants

Reaction Conditions

Reaction Steps

To a −78° C. solution of (6-chloropyridin-3-yl)methanol from Step 1 (7.5 g) and triethylamine (8.7 mL) in dichloromethane (250 mL) was slowly added methanesulphonyl chloride (4.5 mL). The reaction mixture was stirred at 0° C. for 1 hour. Then poured into ice and HCl (1N), adjusted pH at 4 with saturated aqueous disodium hydrogen phosphate and partitioned. The aqueous layer was extracted with dichloromethane (1×150 mL). The combined extracts were washed with brine, dried with magnesium sulfate and the solvent removed in vacuo. The residue was dissolved in DMF (100 mL) and sodium cyanide (2.8 g) was added. The reaction mixture was stirred at room temperature for 3 hours and poured into ice and water (100 mL). Extracted with ethyl acetate (2×100 mL). The combined extracts were washed with brine, dried with magnesium sulfate and the solvent removed in vacuo. The residue was purified by chromatography on SiO2 using ethyl acetate and hexanes (1:5 to 1:2) to yield the title compound.

Provenance & Evidence