Water → 6-Ethyl-2-oxo-1-phenyl-1,2-dihydropyridine-3-carboxylic acid

HRID 2095782Notes

Reaction equation

[CH2:1]([C:3]1[N:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:7](=[O:15])[C:6]([C:16]#N)=[CH:5][CH:4]=1)[CH3:2].[OH-:18].[Na+].[OH2:20]>S(=O)(=O)(O)O>[CH2:1]([C:3]1[N:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:7](=[O:15])[C:6]([C:16]([OH:20])=[O:18])=[CH:5][CH:4]=1)[CH3:2]

Participants

Conditions

Temperature: 120 °C

Procedure

6-Ethyl-2-oxo-1-phenyl-1,2-dihydropyridine-3-carbonitrile (395 mg, 1.76 mmol) was dissolved in conc. sulfuric acid (0.4 mL) and water (0.4 mL), and the mixture was stirred with heating at 120° C. for 7 hr. 1N Aqueous sodium hydroxide solution was added to the reaction solution, and the mixture was washed with ethyl acetate. 1N Hydrochloric acid was added to the aqueous layer, and the mixture was extracted 3 times with ethyl acetate. The combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered, and the solvent was evaporated under reduced pressure. The residue was washed with ethyl acetate to give the title compound (310 mg, 72%) as a colorless solid.

Workup

washthe mixture was washed with ethyl acetate
addition1N Hydrochloric acid was added to the aqueous layer
extractionthe mixture was extracted 3 times with ethyl acetate
washThe combined organic layer was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
customthe solvent was evaporated under reduced pressure
washThe residue was washed with ethyl acetate

Sources & evidence

ORD record: ord-f5dd924ee3ba496badf11f1d708f9a35
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445509B2

Reaction notes

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