Реакция #1515001

Уравнение реакции

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

potassium carbonate

hydrogen peroxide

→

title compound

Выход 80.5%

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

Выход 80.5%

Растворители

dimethylsulfoxide

methylene chloride

Условия реакции

Обработка

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

Методика

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).

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