Water → 1-oxo-2,3-dihydro-1H-indene-5-carbonitrile

HRID 1596424Notes

Reaction equation

HRID 1596424 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2.[C:12]([Cu])#[N:13].O>CN(C)C=O.Cl.[Fe](Cl)(Cl)Cl>[O:11]=[C:7]1[C:8]2[C:4](=[CH:3][C:2]([C:12]#[N:13])=[CH:10][CH:9]=2)[CH2:5][CH2:6]1

Participants

7

Reactant 3

HCID 962WaterHCID 5206955-Bromo-1-indanoneHCID 178418546HCID 178418546, compound

Product 1

HCID 3128961-oxo-2,3-dihydro-1H-indene-5-carbonitrile

Reagents, catalysts & solvents 3

HCID 24380Iron chloride (FeCl3)CatalystHCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Procedure

9.5 g of 5-bromoindan-1-one and 4.93 g of CuCN are suspended in 10 ml of dimethylformamide and the mixture is refluxed for 4 hours. A solution of 18 g of iron(III) chloride in 5 ml of conc. hydrochloric acid with 30 ml of water is added dropwise with stirring to the cooled, dark-brown, viscous suspension and the mixture is then stirred at 70° C. for 30 minutes. The reaction mixture is extracted three times by shaking with 50 ml of toluene, and the combined organic phases are extracted by shaking with 50 ml of 2N hydrochloric acid and 50 ml of 2N sodium hydroxide solution and then washed with water until neutral. The toluene extract is dried over magnesium sulfate and concentrated in vacuo, and the residue is recrystallized from n-heptane. 1-Oxoindan-5-carbonitrile of melting point 123-125° C. is obtained.

Workup

  1. temperaturethe mixture is refluxed for 4 hours
  2. stirringdark-brown, viscous suspension and the mixture is then stirred at 70° C. for 30 minutes
  3. extractionThe reaction mixture is extracted three times
  4. stirringby shaking with 50 ml of toluene
  5. extractionthe combined organic phases are extracted
  6. stirringby shaking with 50 ml of 2N hydrochloric acid and 50 ml of 2N sodium hydroxide solution
  7. washwashed with water until neutral
  8. extractionThe toluene extract
  9. dry with materialis dried over magnesium sulfate
  10. concentrationconcentrated in vacuo
  11. customthe residue is recrystallized from n-heptane

Sources & evidence

ORD record
ord-372bebb8a1c743728e3ccac3b745f399
Source dataset
uspto-grants-2001_09
Patent number
US06291486B1

Reaction notes

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