Reacción #1515001

Ecuación de reacción

4-(adamantan-1-ylmethoxy)-3-(2-methoxypyridin-3-yl)benzonitrile

potassium carbonate

hydrogen peroxide

→

title compound

Rendimiento 80.5%

4-(adamantan-1-ylmethoxy)-3-(2-methoxypyridin-3-yl)benzamide

Rendimiento 80.5%

Disolventes

dimethylsulfoxide

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe volatiles were removed by evaporation in vacuo
2. 2
   workup.ADDITIONThe residue was diluted with water (100 mL)
3. 3
   FiltraciónThe precipitate was collected by filtration
4. 4
   Lavadowashed with water

Procedimiento

To a solution of 4-(adamantan-1-ylmethoxy)-3-(2-methoxypyridin-3-yl)benzonitrile (1.15 g, 3.07 mmol) in dimethylsulfoxide (25 mL) and methylene chloride (25 mL) was added potassium carbonate (0.85 g, 6.15 mmol) followed by addition of 35% hydrogen peroxide aqueous solution (5.30 mL, 61.60 mmol) dropwise. The mixture was stirred at ambient temperature for 4 h, the volatiles were removed by evaporation in vacuo. The residue was diluted with water (100 mL). The precipitate was collected by filtration and washed with water to give the title compound as a colorless solid (0.97 g, 80%): 1H NMR (300 MHz, CDCl3) δ 8.18-8.15 (m, 1H), 7.84-7.79 (m, 1H), 7.71-7.69 (m, 1H), 7.54-7.50 (m, 1H), 6.95-6.91 (m, 2H), 5.85 (br s, 2H), 3.87 (s, 3H), 3.49 (s, 2H), 1.89 (br s, 3H), 1.68-1.37 (m, 12H); MS (ES+) m/z: 393.2 (M+1).

Fuente