Sulfuric Acid → HCID 58158642, compound

HRID 2095870Notes

Reaction equation

HRID 2095870 reaction equation
S(=O)(=O)(O)[OH:2].[F:6][C:7]1[CH:8]=[C:9]([N:14]2[C:19]([CH3:20])=[CH:18][CH:17]=[C:16]([C:21]#N)[C:15]2=[O:23])[CH:10]=[CH:11][C:12]=1[F:13].[OH-:24].[Na+]>O>[F:6][C:7]1[CH:8]=[C:9]([N:14]2[C:19]([CH3:20])=[CH:18][CH:17]=[C:16]([C:21]([OH:2])=[O:24])[C:15]2=[O:23])[CH:10]=[CH:11][C:12]=1[F:13]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 58158497HCID 58158497, compound

Product 1

HCID 58158642HCID 58158642, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Water (7.2 mL) and conc. sulfuric acid (7.2 mL) were added to 1-(3,4-difluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (3.6 g, 14.6 mmol), and the mixture was stirred at 100° C. for 20 hr. The mixture was basified (pH 10) with 8N aqueous sodium hydroxide solution at 0° C. and washed with ethyl acetate. The aqueous layer was acidified (pH 3) with 6N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated under reduced pressure, and the obtained residue was washed with ethyl acetate/hexane (=1/1) and collected by filtration to give the title compound (2.49 g, 64%) as a thin-yellow powder.

Workup

  1. customat 0° C.
  2. washwashed with ethyl acetate
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customThe solvent was evaporated under reduced pressure
  8. washthe obtained residue was washed with ethyl acetate/hexane (=1/1)
  9. filtrationcollected by filtration

Sources & evidence

ORD record
ord-fd78d43b22e1489c9624fe38d1bbdc0a
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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