Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sulfuric Acid | HCID 1118 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | HCID 66968778 | HCID 66968778 | — |
| Reactant | HCID 66969137 | HCID 66969137 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 66968919 | HCID 66968919 | 55% |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08445509B2 |
|---|
| Source dataset | uspto-grants-2013_05 |
|---|
| ORD ID | ord-0be638ac478048d7936b493062882d09 |
|---|
| Source note | uspto-grants-2013_05 |
|---|