2-Methyl-4-methoxypyridine-N-oxide → 4-Methoxy-2-methylpyridine

Temperature

120 °C

To a stirred solution of 4-methoxy-2-methylpyridine 1-oxide (20 g, 0.143 mol) in AcOH (200 mL, sdfine, India), was added Fe (16 g, 0.287 mol, sdfine, India) and the reaction mixture was stirred for 2 h at 120° C. The reaction mixture was concentrated and neutralized with sat'd NaHCO3. EtOAc was added to the mixture and it was filtered through Celite® brand filter agent. The organic layer was separated and the aqueous layer was extracted with EtOAc (3×150 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated to give the title compound as a brown liquid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.33 (d, J=6 Hz, 1H), 6.68-6.64 (m, 2H), 3.84 (s, 3H), 2.52 (s, 3H). MS (ESI, positive ion) m/z: 124.0 (M+H).

1. concentrationThe reaction mixture was concentrated
2. additionEtOAc was added to the mixture and it
3. filtrationwas filtered through Celite® brand
4. filtrationfilter agent
5. customThe organic layer was separated
6. extractionthe aqueous layer was extracted with EtOAc (3×150 mL)
7. dry with materialThe combined organic layers were dried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-1fc9b8c7e57e4e74bcef376ed1d778ed

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09096527B2