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

HRID 2095806Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13]([CH:14]([CH3:16])[CH3:15])=[CH:12][CH:11]=[C:10]([C:17]#N)[C:9]2=[O:19])=[CH:4][CH:3]=1.S(=O)(=O)(O)[OH:21].[OH-:25].[Na+]>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13]([CH:14]([CH3:16])[CH3:15])=[CH:12][CH:11]=[C:10]([C:17]([OH:21])=[O:25])[C:9]2=[O:19])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of 1-(4-fluorophenyl)-6-(1-methylethyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile (604 mg, 2.35 mmol) and water (5 mL) was added conc. sulfuric acid (5 mL) at 0° C., and the mixture was stirred at 100° C. for 14 hr. After cooling to 0° C., the mixture was basified (pH 11) with 8N aqueous sodium hydroxide solution and washed with ethyl acetate. The aqueous layer was acidified (pH 4) with 5N hydrochloric acid and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and filtered, and the solvent was evaporated under reduced pressure to give the title compound (425 mg, 65%) as a pale-yellow solid.

Workup

temperatureAfter cooling to 0° C.
washwashed with ethyl acetate
extractionextracted with ethyl acetate
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
filtrationfiltered
customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-ea2fc65335a8478ca34d273fd34ecce2
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445509B2

Reaction notes

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