Lithium Hydroxide → 2-(2-Fluoro-4-iodophenylamino)-1,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid

HRID 1186761Notes

Reaction equation

HRID 1186761 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[N:11]([CH3:22])[C:12](=[O:21])[C:13]([CH3:20])=[CH:14][C:15]=1[C:16]([O:18]C)=[O:17].C1COCC1.[Li+].[OH-]>O>[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[N:11]([CH3:22])[C:12](=[O:21])[C:13]([CH3:20])=[CH:14][C:15]=1[C:16]([OH:18])=[O:17]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 57636896Methyl 2-(2-fluoro-4-iodophenylamino)-1,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxylate

Product 1

HCID 441892192-(2-Fluoro-4-iodophenylamino)-1,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxylic acidYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 100 mL round-bottom flask was charged with methyl 2-(2-fluoro-4-iodophenylamino)-1,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxylate (2.38 g, 6.72 mmol) and THF (80 mL). To the mixture was added LiOH (20 mmol) previously dissolved in 30 mL of H2O and the reaction was stirred at room temperature for 72 hours. The organic solvent was removed under reduced pressure and the resulting aqueous layer was acidified with 1N aq. HCl. The precipitate was filtered and dried under vacuum to afford the title compound as a white solid (2.12 g, 92%).

Workup

  1. customThe organic solvent was removed under reduced pressure
  2. filtrationThe precipitate was filtered
  3. customdried under vacuum

Sources & evidence

ORD record
ord-19297c0184814885b772318a7a79c57d
Source dataset
uspto-grants-2014_03
Patent number
US08673919B2

Reaction notes

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