Reacción #66517

Ecuación de reacción

3-Methoxyaniline

picolinic acid

EDCI.HCl

Et3N

hydroxybenzotriazole

→

N-(3-methoxyphenyl)picolinamide

Rendimiento 90.1%

Disolventes

DCM

Condiciones de reacción

Tratamiento posterior

1. 1
   LavadoThe organic phase was washed with a saturated solution of NaHCO3 and with brine
2. 2
   Secadowas dried over MgSO4
3. 3
   Filtraciónwas filtered
4. 4
   Concentraciónwas concentrated under reduced pressure
5. 5
   OtroThe crude product was purified by flash chromatography over silica gel

Procedimiento

According to Scheme 1 Method B: 3-Methoxyaniline (1.62 mmol, 0.18 mL) was added to a solution of picolinic acid (1.62 mmol, 0.20 g), EDCI.HCl (2.44 mmol, 0.47 g), Et3N (3.25 mmol, 0.45 mL), hydroxybenzotriazole (1.95 mmol, 0.30 g) in DCM (6 mL) at room temperature. The reaction mixture was stirred at 50° C. for 12 hours. The organic phase was washed with a saturated solution of NaHCO3 and with brine, was dried over MgSO4, was filtered and was concentrated under reduced pressure. The crude product was purified by flash chromatography over silica gel using cyclohexane/AcOEt (90:10) as eluent to afford N-(3-methoxyphenyl)picolinamide (1.46 mmol, 0.33 g, 90%) as an orange liquid.

Fuente