Sulfuric Acid → 1-(4-Fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylic acid

HRID 2095784Notes

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])=[CH:4][CH:3]=1.[OH-:18].[Na+].S(=O)(=O)(O)[OH:21]>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:21])=[O:18])[C:9]2=[O:17])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

1-(4-Fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (3 g, 13.1 mmol) was dissolved in conc. sulfuric acid (6.0 mL) and water (6.0 mL), and the mixture was stirred with heating at 120° C. for 20 hr. 8N Aqueous sodium hydroxide solution was added to the reaction solution, and the mixture was washed with ethyl acetate. 2N hydrochloric acid was added to the aqueous layer, and the mixture was extracted twice 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 diethyl ether and collected by filtration to give the title compound (2.41 g, 74%) as a pale-brown solid.

Workup

washthe mixture was washed with ethyl acetate
addition2N hydrochloric acid was added to the aqueous layer
extractionthe mixture was extracted twice 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 diethyl ether
filtrationcollected by filtration

Sources & evidence

ORD record: ord-7627c377691946cc8cd2cc8db824111b
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445509B2

Reaction notes

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