Toluene → 3-Acetyl-6-methylpyridine

Temperature

80 °C

50 g of methyl 6-methylnicotinate was dissolved in 200 ml of ethyl acetate; 60% NaH 26.5 g, toluene 400 ml and DMF 34 ml were added to a three-necked bottle, 10% methyl 6-methylnicotinate ethyl acetate solution 20 ml was added, heated to 80° C., stirred for 0.5 h. To the reaction bottle, the residual methyl 6-methylnicotinate ethyl acetate solution was added dropwise slowly within about 1.5 h. After addition, the reaction was conducted at 80° C. for 8 h. The reaction stopped, cooled to room temperature. 300 ml of water was added to the reaction bottle, skimmed, the water layer was extracted with ethyl acetate three times, 200 ml per time. All ethyl acetate layers were combined, distillated at a reduced pressure to evaporate ethyl acetate, then 10% H2SO4 aqueous solution 400 ml was added, heated to 110° C., refluxed for 2 h. The reaction was then stopped, cooled to room temperature. Solid K2CO3 was used to adjust PH to 9, suction filtration was performed, the filter cake was washed with ethyl acetate. The filtrate was extracted with ethyl acetate four times, combined and rotary evaporated to dry, to obtain 35 g of 2-methyl-5-acetylpyridine, yield was about 65%.

1. additionwas added
2. additionAfter addition
3. waitthe reaction was conducted at 80° C. for 8 h
4. temperaturecooled to room temperature
5. extractionthe water layer was extracted with ethyl acetate three times, 200 ml per time
6. customto evaporate ethyl acetate
7. addition10% H2SO4 aqueous solution 400 ml was added
8. temperatureheated to 110° C.
9. temperaturerefluxed for 2 h
10. temperaturecooled to room temperature
11. filtrationto 9, suction filtration
12. washthe filter cake was washed with ethyl acetate
13. extractionThe filtrate was extracted with ethyl acetate four times
14. customrotary evaporated
15. customto dry

ORD record

ord-5702134106ae4ee1823488ad433434f3

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09149467B2