Ethanol → HCID 68918893, compound

HRID 2111625Notes

Reaction equation

HRID 2111625 reaction equation
C(O)C.[CH3:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[CH3:14])[C:10](=[O:15])[N:9]([C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)[CH:8]2[CH2:23][CH2:24]OS(C)(=O)=O.[C-:30]#[N:31].[K+]>O>[CH3:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[CH3:14])[C:10](=[O:15])[N:9]([C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)[CH:8]2[CH2:23][CH2:24][C:30]#[N:31]

Participants

5

Reactant 3

HCID 702EthanolHCID 9032Potassium CyanideHCID 87623111HCID 87623111, compound

Product 1

HCID 68918893HCID 68918893, compoundYield 97.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 80% ethanol solution of the product of above-mentioned (4-b) (0.23 g, 0.63 mmol) was added potassium cyanide (0.12 g, 1.9 mmol) and heated under reflux for 4 hrs. To the reaction solution was added water, and extracted with ethyl acetate. The extract was washed with water, dried and the solvent was distilled away under reduced pressure to give 0.19 g of 5,6-dimethyl-2-(4-fluorophenyl)-3-cyanoethylisoindolin-1-one [IUPAC name: 3-[2-(4-fluorophenyl)-5,6-dimethyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl]propanenitrile].

Workup

  1. temperatureheated
  2. temperatureunder reflux for 4 hrs
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. customdried
  6. distillationthe solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-89ebd25ae986423baec4b7dd6d22bf94
Source dataset
uspto-grants-2009_04
Patent number
US07521451B2

Reaction notes

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