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

HRID 2095804Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:14]([CH3:15])=[CH:13][CH:12]=[C:11]([C:16]#N)[C:10]1=[O:18].BrC1C=C(F)C=CC=1N1C=CC(C)=C(C#N)C1=[O:36].S(=O)(=O)(O)O.[OH-:42].[Na+]>O>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:14]([CH3:15])=[CH:13][CH:12]=[C:11]([C:16]([OH:36])=[O:42])[C:10]1=[O:18]

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of 1-(2-bromo-4-fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile, 1-(2-bromo-4-fluorophenyl)-4-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (2.00 g, 6.51 mmol) and water (10 mL) was added conc. sulfuric acid (10 mL) at 0° C., and the mixture was stirred at 100° C. for 16 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. The obtained residue was washed with diethyl ether and collected by filtration to give the title compound (1.12 g, 53%) as a white powder.

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
washThe obtained residue was washed with diethyl ether
filtrationcollected by filtration

Sources & evidence

ORD record: ord-c29da9e682cf435ea19d2c0b2e3b5545
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445509B2

Reaction notes

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