Chloroform → 3-Chloromethyl-2-methyl-pyridine 1-oxide

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 crude 3-hydroxymethyl-2-methyl-pyridine of Step B (1.35 g, 9.53 mmol) in chloroform (50 mL) was added 90% m-chloroperbenzoic acid (2.0 g, 10.4 mmol). After stirring overnight at room temperature, an additional quantity of 90% m-chloroperbenzoic acid (1.0 g, 5.2 mmol) was added. The reaction mixture was stirred for an additional 3 hours and then quenched with saturated aqueous sodium bicarbonate. The organic layer was washed with water, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give a yellow solid. Purification by flash chromatography using a solvent system of 3% methanol in chloroform provided 0.85 g of the title compound as a brown-orange amorphous solid.

1. customPrepared essentially
2. stirringThe reaction mixture was stirred for an additional 3 hours
3. customquenched with saturated aqueous sodium bicarbonate
4. washThe organic layer was washed with water
5. dry with materialdried over anhydrous sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customto give a yellow solid
9. customPurification by flash chromatography

ORD record

ord-bcc520b7612f46b4a95bee502266bc4e

Source dataset

uspto-grants-2006_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07064120B2