Water → 6-Ethyl-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid

HRID 2095856Notes

Reaction equation

HRID 2095856 reaction equation
[CH2:1]([C:3]1[N:8]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[C:7](=[O:16])[C:6]([C:17]#N)=[CH:5][CH:4]=1)[CH3:2].[OH2:19].[OH-:20].[Na+]>S(=O)(=O)(O)O>[CH2:1]([C:3]1[N:8]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[C:7](=[O:16])[C:6]([C:17]([OH:20])=[O:19])=[CH:5][CH:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 669688016-Ethyl-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile

Product 1

HCID 581586366-Ethyl-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acidYield 78%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 6-ethyl-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile (410 mg, 1.69 mmol) in conc. sulfuric acid (2 mL)/water (2 mL) was stirred at 120° C. for 17 hr. The reaction solution was allowed to cool to room temperature, 6N aqueous sodium hydroxide solution was added, and the aqueous layer was washed with ethyl acetate. 1N Hydrochloric acid was added to the aqueous layer, and the precipitate was collected by filtration and washed with water to give the title compound (345 mg, 78%) as a white solid.

Workup

  1. washthe aqueous layer was washed with ethyl acetate
  2. addition1N Hydrochloric acid was added to the aqueous layer
  3. filtrationthe precipitate was collected by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-9c27cc78d92b49f5b8c9fa6e908c254b
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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