反应详情

Triethylamine (7.6 mL, 54.651 mmol) was added slowly to a mixture of 3-methyl-4-nitrobenzoic acid (5 g, 27.326 mmol), N,O-dimethylhydroxylamine hydrochloride (2.99 g, 30.058 mmol), and EDCI (6.28 g, 32.791 mmol) in DCM (30 mL). The mixture was stirred at room temperature overnight, quenched with saturated aqueous NaHCO3 and stirred at room temperature for 30 minutes. Water (50 mL) was added followed by additional DCM. The mixture was stirred for 10 minutes and layers were separated. The aqueous layer was again extracted with DCM. The combined organic layer was dried over Na2SO4, then filtered. The solvent was removed and the residual oil chromatographed (DCM/EtOAc) to provide the product as a white solid.

1. customquenched with saturated aqueous NaHCO3
2. stirringstirred at room temperature for 30 minutes
3. additionWater (50 mL) was added
4. stirringThe mixture was stirred for 10 minutes
5. customlayers were separated
6. extractionThe aqueous layer was again extracted with DCM
7. dry with materialThe combined organic layer was dried over Na2SO4
8. filtrationfiltered
9. customThe solvent was removed
10. customthe residual oil chromatographed (DCM/EtOAc)