Reaction #2487463

Reaction equation

Water

sodium hydrogen carbonate

hydroxylamine hydrochloride

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

→

title compound

Yield 99.1%

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

Yield 99.1%

Solvents

dimethylsulfoxide

Conditions

Workup

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

Procedure

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