Thionyl Chloride → 3-(Chloromethyl)-2-methylpyridine

Prepared essentially according to the procedure of I. M. Bell et al., J. Med. Chem. 41, 2146–2163 (1998). To a stirred solution of the 3-hydroxymethyl-2-methyl-pyridine of Step A (2.5 g, 20.3 mmol) in dichloromethane (100 mL) was added thionyl chloride (15 mL, 206 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 1.35 g of the title compound as an orange oil which was immediately used in the next step.

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

ORD record

ord-63411dbfd2bd46c98b5d94efc8f936c2

Source dataset

uspto-grants-2006_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07064120B2