Methyl iodide → 5-Methoxy-2-methylpyridine

To sodium hydroxide (50% oil dispersion, 43.2 g, 21.6 g of active NaH, 900 mmol), prewashed in dry hexane, in 800 ml of dimethylformamide (DMF) is added 5-hydroxy-2-methylpyridine (98.8 g, 906 mmol) in 700 ml of DMF at 15° and over 0.75 hour. The reaction is allowed to warm to RT and is stirred for 2 hours. It is then cooled to 10°, and methyliodide is added over 0.5 hour. The reaction is again allowed to warm to RT and is stirred overnight. It is then filtered through celite, and the solid is washed with chloroform, filtered and rotoevaporated. The resulting solid is washed with chloroform 3×, and is stirred with chloroform overnight. It is filtered and rotoevaporated, after which ether is added, followed by 10% sodium hydroxide and water. The mixture is extracted with ether (3×). The combined ether extracts are washed with water and with brine, dried over calcium sulfate, filtered and rotoevaporated to give 5 -methoxy-2-methylpyridine.

1. temperatureIt is then cooled to 10°
2. temperatureto warm to RT
3. stirringis stirred overnight
4. filtrationIt is then filtered through celite
5. washthe solid is washed with chloroform
6. filtrationfiltered
7. washThe resulting solid is washed with chloroform 3×
8. stirringis stirred with chloroform overnight
9. filtrationIt is filtered
10. additionafter which ether is added
11. extractionThe mixture is extracted with ether (3×)
12. washThe combined ether extracts are washed with water and with brine
13. dry with materialdried over calcium sulfate
14. filtrationfiltered

ORD record

ord-44a5c97afc72498496a0c0c1db39cd3b

Source dataset

uspto-grants-1983_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04406690