Reaktion #66517

Reaktionsgleichung

3-Methoxyaniline

picolinic acid

EDCI.HCl

Et3N

hydroxybenzotriazole

→

N-(3-methoxyphenyl)picolinamide

Ausbeute 90.1%

Lösungsmittel

DCM

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle