Water → 1-(2,4-Difluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylic acid

HRID 2095852Notes

Reaction equation

HRID 2095852 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:14]([CH3:15])=[CH:13][CH:12]=[C:11]([C:16]#N)[C:10]1=[O:18].[OH2:19].[OH-:20].[Na+]>S(=O)(=O)(O)O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:14]([CH3:15])=[CH:13][CH:12]=[C:11]([C:16]([OH:20])=[O:19])[C:10]1=[O:18]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 581584621-(2,4-Difluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile

Product 1

HCID 581586271-(2,4-Difluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylic acidYield 93%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 1-(2,4-difluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (600 mg, 2.44 mmol) in conc. sulfuric acid (3 mL)/water (3 mL) was stirred at 120° C. for 17 hr. The reaction solution was allowed to cool to room temperature, and alkalified with 8N aqueous sodium hydroxide solution. The aqueous layer was washed with ethyl acetate. The aqueous layer was acidified with 2N hydrochloric acid and the precipitate was collected by filtration and washed with water to give the title compound (600 mg, 93%) as a white solid.

Workup

  1. washThe aqueous layer was washed with ethyl acetate
  2. filtrationthe precipitate was collected by filtration
  3. washwashed with water

Sources & evidence

ORD record
ord-09e3cfaf551a42c4bf70a6d7eb51e859
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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