Sulfuric Acid → HCID 58158471, compound

HRID 2095777Notes

Reaction equation

HRID 2095777 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13]([CH3:14])=[CH:12][CH:11]=[C:10]([C:15]#N)[C:9]2=[O:17])=[C:4]([CH3:18])[CH:3]=1.S(=O)(=O)(O)[OH:20].[OH-:24].[Na+]>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13]([CH3:14])=[CH:12][CH:11]=[C:10]([C:15]([OH:20])=[O:24])[C:9]2=[O:17])=[C:4]([CH3:18])[CH:3]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 66968917HCID 66968917, compound

Product 1

HCID 58158471HCID 58158471, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

1-(4-fluoro-2-methylphenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (590 mg, 2.9 mmol) was suspended in water (3.0 mL), conc. sulfuric acid (3.0 mL) was slowly added dropwise. The mixture was stirred overnight at 100° C., and allowed to cool to room temperature. The reaction system was basified with aqueous sodium hydroxide solution (8N) and washed with ethyl acetate. The aqueous layer was acidified with hydrochloric acid (1N), and extracted twice with ethyl acetate. The mixed organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. Hexane-ethyl acetate was added to the residue, and the resulting precipitate was collected by filtration to give the title compound (480 mg, 75%) as a white solid.

Workup

  1. temperatureto cool to room temperature
  2. washwashed with ethyl acetate
  3. extractionextracted twice with ethyl acetate
  4. dry with materialThe mixed organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. additionHexane-ethyl acetate was added to the residue
  7. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-e3854a02da0b49a392a228a3ad7d92c9
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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