m-Chloroperbenzoic acid → 2-Chloro-6-methylpyridine 1-oxide

Temperature

40 °C

2-Chloro-6-methylpyridine (12.76 g, 0.1 mol) was dissolved together with m-chloroperbenzoic acid (17.56 g, 0.15 mol) in DCM (100 ml) and stirred at 40° C. for 90 minutes. The heating bath was removed and stirring was continued overnight at room temperature. The reaction mixture was quenched with saturated sodium thiosulfate solution and the pH was adjusted to 8 with 1M NaOH. The phases were separated, the aqueous phase extracted with DCM and the combined organic phases were dried over magnesium sulfate. The solvent was removed under reduced pressure and unreacted 2-chloro-6-methylpyridine was removed by distillation (2 mbar, 65° C.). 2-Chloro-6-methyl-pyridine 1-oxide was obtained as residue (6.0 g of a yellow oil, 0.042 mol, 42%). MS (ESI) m/z=144.0 [M+1]+.

1. customThe heating bath was removed
2. stirringstirring
3. waitwas continued overnight at room temperature
4. customThe reaction mixture was quenched with saturated sodium thiosulfate solution
5. customThe phases were separated
6. extractionthe aqueous phase extracted with DCM
7. dry with materialthe combined organic phases were dried over magnesium sulfate
8. customThe solvent was removed under reduced pressure and unreacted 2-chloro-6-methylpyridine
9. customwas removed by distillation (2 mbar, 65° C.)

ORD record

ord-8324e3b058454acab71c208d7548a50b

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08877934B2