Reaction #66517

Reaction equation

3-Methoxyaniline

picolinic acid

EDCI.HCl

Et3N

hydroxybenzotriazole

→

N-(3-methoxyphenyl)picolinamide

Yield 90.1%

Solvents

DCM

Conditions

Workup

1. 1
   WashThe organic phase was washed with a saturated solution of NaHCO3 and with brine
2. 2
   Dryingwas dried over MgSO4
3. 3
   Filtrationwas filtered
4. 4
   Concentrationwas concentrated under reduced pressure
5. 5
   OtherThe crude product was purified by flash chromatography over silica gel

Procedure

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.

Source