Sulfuric Acid → HCID 66968919, compound
Reaction equation
[Cl: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].ClC1C=C(F)C=CC=1N1C=CC(C)=C(C#N)C1=[O:36].S(=O)(=O)(O)O.[OH-:42].[Na+]>O>[Cl: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
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
To a mixture of 1-(2-chloro-4-fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile, 1-(2-chloro-4-fluorophenyl)-4-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (0.75 g, 3.80 mmol) and water (5 mL) was added conc. sulfuric acid (5 mL) at 0° C., and the mixture was stirred at 100° C. for 18 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 (588 mg, 55%) as a white 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
- washThe obtained residue was washed with diethyl ether
- filtrationcollected by filtration
Sources & evidence
- ORD record
- ord-0be638ac478048d7936b493062882d09
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08445509B2
Reaction notes
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