Reaction #2275695

Reaction equation

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

MeOH

sodium hydroxide

→

desired product

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

Conditions

Workup

1. 1
   Temperaturethe reaction mixture is refluxed for 16 hours
2. 2
   OtherThe solvent is removed under reduced pressure
3. 3
   OtherThe precipitate that results
4. 4
   Filtrationis collected by filtration
5. 5
   Washwashed with H2O (10 mL)
6. 6
   Otherdried overnight in a vacuum oven

Procedure

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]+.

Source