Water → HCID 117770148, compound

HRID 1526338Notes

Reaction equation

HRID 1526338 reaction equation
Br[CH2:2][C:3]1[N:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[Cl:15])[C:7](=[O:16])[C:6]([C:17]#[N:18])=[C:5]([Cl:19])[CH:4]=1.[C:20]([O-:23])(=[O:22])[CH3:21].[Na+].O>CC(C)=O>[C:20]([O:23][CH2:2][C:3]1[N:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[Cl:15])[C:7](=[O:16])[C:6]([C:17]#[N:18])=[C:5]([Cl:19])[CH:4]=1)(=[O:22])[CH3:21]

Participants

5

Reactant 3

HCID 962WaterHCID 517045Sodium AcetateHCID 117770794HCID 117770794, compound

Product 1

HCID 117770148HCID 117770148, compoundYield 46.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 6-(bromomethyl)-4-chloro-1-(2-chlorophenyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile obtained in Step F (1.53 g) in acetone (42.7 mL) was added sodium acetate (1.75 g) at room temperature. The reaction mixture was stirred at 70° C. for 8 hr, and cooled to room temperature. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (670 mg).

Workup

  1. temperaturecooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-dad59f43e39c469ba8200805b319a21e
Source dataset
uspto-grants-2015_07
Patent number
US09085578B2

Reaction notes

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