Oxalyl chloride → (2,6-Dichloropyridin-3-yl)methanol

Temperature

60 °C

To a solution of 2,6-dichloronicotinic acid (10 g) in MeOH (300 mL) was added oxalyl chloride (5.5 mL) dropwise at 0° C. The mixture was heated to 60° C. for a couple of hours until reaction complete. Upon concentration, the residue was dissolved in ether and added lithium aluminum hydride (2.3 g) slowly at 0° C. The reaction was stirred at 0° C. for 1 h and added water (2.3 mL) dropwise to quench excess lithium aluminum hydride. The resulting mixture was added 15% NaOH (2.3 mL) slowly, water (6.9 mL) and stirred at 0° C. for an additional 1 h. The slush solution was filtered through celite and washed with ether. The filtrate was concentrated to give the title compound (6.5 g).

1. concentrationUpon concentration
2. dissolutionthe residue was dissolved in ether
3. additionadded lithium aluminum hydride (2.3 g) slowly at 0° C
4. additionadded water (2.3 mL) dropwise
5. customto quench excess lithium aluminum hydride
6. additionThe resulting mixture was added 15% NaOH (2.3 mL) slowly
7. stirringwater (6.9 mL) and stirred at 0° C. for an additional 1 h
8. filtrationThe slush solution was filtered through celite
9. washwashed with ether
10. concentrationThe filtrate was concentrated

ORD record

ord-e27ae3170c334ff288a8f755ef3b7142

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07879875B2