Hydrochloric Acid → (2-Chloropyridin-4-yl)methanol

78.78 g of 2-chloroisonicotinic acid are added, under argon, portionwise, to 300 mL of a 2M solution of dimethyl sulphide-borane in tetrahydrofuran. The reaction mixture is stirred for 17 hours at room temperature and then treated successively with 20 mL of water dropwise and 20 mL of 5N hydrochloric acid. 300 mL of ethyl acetate are then added, the phases are separated and the organic phase is washed with three times 100 mL of saturated sodium chloride solution, dried over magnesium sulphate and filtered. The filtrate is then concentrated under reduced pressure to give 68.6 g of 2-chloro-4-hydroxymethylpyridine in the form of a pale yellow solid.

1. customthe phases are separated
2. washthe organic phase is washed with three times 100 mL of saturated sodium chloride solution
3. dry with materialdried over magnesium sulphate
4. filtrationfiltered
5. concentrationThe filtrate is then concentrated under reduced pressure

ORD record

ord-77fa113454f84d7fa89cad917f908925

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07935819B2