Réaction #2487463

Équation de réaction

Water

sodium hydrogen carbonate

hydroxylamine hydrochloride

6-(5-methoxy-2-phenylindol-1-ylmethyl)pyridine-2-carbonitrile

→

title compound

Rendement 99.1%

6-(5-Methoxy-2-phenylindol-1-ylmethyl)pyridine-2-carboxamidoxime

Rendement 99.1%

Solvants

dimethylsulfoxide

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGby stirring at 80° C. overnight
2. 2
   Extractionfollowed by extraction with ethyl acetate
3. 3
   LavageThe organic layer was washed with water and saturated brine
4. 4
   Séchagedried over anhydrous magnesium sulfate
5. 5
   Concentrationconcentrated under reduced pressure

Mode opératoire

To a suspension of hydroxylamine hydrochloride (233 mg) in dimethylsulfoxide (1.7 mL) was added sodium hydrogen carbonate (338 mg), and this mixture was stirred at 50° C. for 1 hour. Subsequently, 6-(5-methoxy-2-phenylindol-1-ylmethyl)pyridine-2-carbonitrile (114 mg) was added thereto, followed by stirring at 80° C. overnight. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain the title compound (124 mg). 1H-NMR (DMSO-d6) δ ppm: 3.76 (3H, s), 5.51 (2H, s), 5.65 (2H, br s), 6.59 (1H, s), 6.70-6.85 (2H, m), 7.11 (1H, d, J=2.4 Hz), 7.32 (1H, d, J=8.9 Hz), 7.35-7.70 (7H, m), 9.92 (1H, s).

Source