N,N-Dimethylaniline → N-(4,6-Dimethyl-3-nitro-2-pyridinyl)acetamide

Temperature

70 °C

A mixture of 2-amino-4,6-dimethyl-3-nitropyridine (14.91 g) and N,N-dimethylaniline (80 ml) was heated at 70° C. To the solution was added dropwise acetyl chloride at 70° C. and the mixture was stirred at 70° C. for 2.5 hours. To the reaction mixture was added ethyl acetate(500 ml). The organic layer was separated. and washed with water three times and brine. The solution was dried over magnesium sulfate and the solvent was evaporated in vacuo. The residue was dissolved in hot isopropyl ether (200 ml), and cooled to ambient temperature. After the mixture was cooled in an ice bath for an hour, the resulting solid collected by filtration, was washed with cold isopropyl ether, purified by flash column chromatography on silica gel eluted by a mixture of ethyl acetate and n-hexane (1:9 then 2:1) to yield a brown oil and the oil was dissolved methanol(40 ml). To the solution was added saturated sodium bicarbonate (10 ml), and stirred at room temperature for 70 minutes. The mixture was diluted with ethy acetate, organic layer was separated, and the aqueous layer was extracted with ethy acetate. The combined ethyl acetate layer was washed with water, dried over magnesium sulfate, and concentated in vacuo. To the residue was added diisopropyl ether (50 ml). After cooling, the solid was collected by filtration and washed diisopropyl ether to give 2-acetylamino-4,6-dimethyl-3-nitropyridine(5.56 g) as colorless powder.

1. customThe organic layer was separated
2. washand washed with water three times and brine
3. dry with materialThe solution was dried over magnesium sulfate
4. customthe solvent was evaporated in vacuo
5. dissolutionThe residue was dissolved in hot isopropyl ether (200 ml)
6. temperaturecooled to ambient temperature
7. temperatureAfter the mixture was cooled in an ice bath for an hour
8. filtrationthe resulting solid collected by filtration
9. washwas washed with cold isopropyl ether
10. custompurified by flash column chromatography on silica gel
11. washeluted by a mixture of ethyl acetate and n-hexane (1:9
12. custom2:1) to yield a brown oil
13. stirringstirred at room temperature for 70 minutes
14. customwas separated
15. extractionthe aqueous layer was extracted with ethy acetate
16. washThe combined ethyl acetate layer was washed with water
17. dry with materialdried over magnesium sulfate
18. additionTo the residue was added diisopropyl ether (50 ml)
19. temperatureAfter cooling
20. filtrationthe solid was collected by filtration
21. washwashed diisopropyl ether

ORD record

ord-93ad09d00ef04438bbe9314e2487ab2a

Source dataset

uspto-grants-1994_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05354759