Thionyl Chloride → 3-(Chloromethyl)-1-oxo-1lambda~5~-pyridine

To a solution of 3-hydroxymethyl-pyridine N-oxide (1.0 g, 8.0 mmol) in dichloromethane (40 mL) was added thionyl chloride (10 mL, 137 mmol). After stirring for 2 hours, the reaction mixture was concentrated in vacuo. The residue was partitioned between dichloromethane and saturated aqueous sodium bicarbonate. The aqueous layer was repeatedly extracted with dichloromethane. The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give 0.60 g of the title product as a white solid, m.p. 133–137° C.

1. concentrationthe reaction mixture was concentrated in vacuo
2. customThe residue was partitioned between dichloromethane and saturated aqueous sodium bicarbonate
3. extractionThe aqueous layer was repeatedly extracted with dichloromethane
4. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo

ORD record

ord-2ba5d0038e8c4c8ebaa02ae350092f4b

Source dataset

uspto-grants-2006_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07064120B2