N,N-Diethylaniline → 2-Chloro-3-methoxypyridine

3-methoxy-2-(1H)pyridone, 10 g. (0.08 mole), 12.3 g. (0.08 mole) of phosphorus oxychloride, and 11.9 g. (0.08 mole) of N,N-diethylaniline are combined in a suitable reaction vessel and heated at reflux for 20 hrs. The reaction mixture was allowed to cool, and was then mixed with 200 ml. of water and ice. The aqueous mixture was extracted with ether and the extracts dried over magnesium sulfate. The drying agent was then removed by filtration and the solvent was removed from the filtrate by distillation in vacuo. The residue was extracted with 160 ml. of boiling hexane and the hexane extracts decanted from the residue while still hot. The hexane solution was cooled in ice resulting in precipitation of the desired produce, weight 7.5 g., m.p. 46°-48°.

1. temperatureheated
2. temperatureat reflux for 20 hrs
3. temperatureto cool
4. additionwas then mixed with 200 ml
5. extractionThe aqueous mixture was extracted with ether
6. dry with materialthe extracts dried over magnesium sulfate
7. customThe drying agent was then removed by filtration
8. customthe solvent was removed from the filtrate by distillation in vacuo
9. extractionThe residue was extracted with 160 ml
10. customof boiling hexane and the hexane extracts decanted from the residue while still hot
11. temperatureThe hexane solution was cooled in ice resulting in precipitation of the
12. customdesired produce

ORD record

ord-9788e01648cd4143bdcc3ce8ea616435

Source dataset

uspto-grants-1981_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04305944