Water → 5-Cyano-2,3'-bipyridine-6'-carboxylic acid

Reaction equation

[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:10]=[N:11][C:12]([C:15]([O:17]C)=[O:16])=[CH:13][CH:14]=2)=[N:7][CH:8]=1)#[N:2].O.[Li+].[OH-]>O1CCCC1>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:10]=[N:11][C:12]([C:15]([OH:17])=[O:16])=[CH:13][CH:14]=2)=[N:7][CH:8]=1)#[N:2]

Participants

Procedure

To a 250 ml flask was added methyl 5-cyano-2,3′-bipyridine-6′-carboxylate (950 mg, 3.57 mmol), water (9.5 ml), tetrahydrofuran (38.4 ml) and LiOH (86 mg, 3.57 mmol). The mixture was stirred for 30 min, diluted with tetrahydrofuran (200 ml) and cooled to 0° C. (ice water batch). After an additional 30 min, the resulting suspension was filtered, washed with THF and dried under reduced pressure to afford the desired product as a light brown powder. LCMS (m/z): 226.1 (M+H).