Water → 1-(4-Fluorophenyl)-2-oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carboxylic acid

HRID 2095854Notes

Reaction equation

HRID 2095854 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:11]=[C:10]([C:18]#N)[C:9]2=[O:20])=[CH:4][CH:3]=1.[OH2:21].[OH-:22].[Na+]>S(=O)(=O)(O)O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:11]=[C:10]([C:18]([OH:22])=[O:21])[C:9]2=[O:20])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 581584831-(4-Fluorophenyl)-2-oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carbonitrile

Product 1

HCID 581584761-(4-Fluorophenyl)-2-oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carboxylic acidYield 75%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 1-(4-fluorophenyl)-2-oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carbonitrile (200 mg, 0.709 mmol) in conc. sulfuric acid (1.5 mL)/water (1.5 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 filtered and washed with water to give the title compound (160 mg, 75%) 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 filtered
  4. washwashed with water

Sources & evidence

ORD record
ord-afbc9741b5b44a2999dafb74706d6b29
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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