Реакция #2275695

Уравнение реакции

3,5-bis-benzyloxy-pyridine-2-carbonitrile

MeOH

sodium hydroxide

→

desired product

3,5-bis-benzyloxy-pyridine-2-carboxylic acid

Условия реакции

Обработка

1. 1
   Температураthe reaction mixture is refluxed for 16 hours
2. 2
   ДругоеThe solvent is removed under reduced pressure
3. 3
   ДругоеThe precipitate that results
4. 4
   Фильтрацияis collected by filtration
5. 5
   Промывкаwashed with H2O (10 mL)
6. 6
   Другоеdried overnight in a vacuum oven

Методика

To a solution of 3,5-bis-benzyloxy-pyridine-2-carbonitrile, 1, (26.0 g, 82.3 mmol) in MeOH (217 mL) is added 30% w/v sodium hydroxide (320 mL) and the reaction mixture is refluxed for 16 hours. The solvent is removed under reduced pressure and the resulting suspension is acidified with conc. HCl until the pH is between 1 and 2. The precipitate that results is collected by filtration, washed with H2O (10 mL) and dried overnight in a vacuum oven to afford 30 g (quantitative) of the desired product as the hydrochloride salt. 1H NMR (250 MHz, DMSO-d6) δ ppm 8.02 (1H, d, J=2.4 Hz), 7.29-7.53 (11H, m), 5.96 (1H, br s), 5.28 (4H, s). HPLC-MS: m/z 336 [M+H]+.

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