反应详情

To a suspension of 2-(trifluoromethyl)isonicotinic acid (1.03 g, 5.39 mmol), N,O-dimethylhydroxylamine hydrochloride (0.800 g, 8.20 mmol) and N′(ethylcarbonimidoyl)-N,N-dimethyl-1,3-propanediamine hydrochloride (EDCI, 1.35 g, 7.04 mmol) in CH2Cl2 (30 mL) was added Et3N (1.90 mL, 13.7 mmol), and the mixture immediately turned clear. After stirring at room temperature overnight, NH4Cl (aqueous) was added. The mixture was stirred vigorously for a while, and white solid was then filtered off. The organic layer was separated, and the aqueous layer was extracted with CH2Cl2. The combined organic phases were washed with brine, and the aqueous layer was back extracted with CH2Cl2. The organic phases were combined, dried (Na2SO4), filtered, concentrated, and purified by flash column chromatography (40 g silica gel column, 40-70% EtOAc in heptanes) to afford the title compound as a clear oil.

1. stirringThe mixture was stirred vigorously for a while, and white solid
2. filtrationwas then filtered off
3. customThe organic layer was separated
4. extractionthe aqueous layer was extracted with CH2Cl2
5. washThe combined organic phases were washed with brine
6. extractionthe aqueous layer was back extracted with CH2Cl2
7. dry with materialdried (Na2SO4)
8. filtrationfiltered
9. concentrationconcentrated
10. custompurified by flash column chromatography (40 g silica gel column, 40-70% EtOAc in heptanes)