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

HRID 2098454Notes

Reaction equation

HRID 2098454 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

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 58286497Methyl 5-cyano-2,3'-bipyridine-6'-carboxylate

Product 1

HCID 582865945-Cyano-2,3'-bipyridine-6'-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

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).

Workup

  1. waitAfter an additional 30 min
  2. filtrationthe resulting suspension was filtered
  3. washwashed with THF
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-b999a10f9a604241b5d1d6d500c4f2a8
Source dataset
uspto-grants-2013_05
Patent number
US08450484B2

Reaction notes

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