Sodium Cyanide → AGN-PC-00FAW9

HRID 277447Notes

Reaction equation

HRID 277447 reaction equation
[C-:1]#[N:2].[Na+].Cl[CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Cl:14])[CH:11]=2)[C:6]1=[O:15]>CN(C)C=O.O>[C:1]([CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Cl:14])[CH:11]=2)[C:6]1=[O:15])#[N:2]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 11019906HCID 11019906, compound

Product 1

HCID 11745457AGN-PC-00FAW9Yield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
50 °C

Procedure

10.4 g of sodium cyanide were dissolved in a mixture of 100 ml of dimethylformamide and 6 ml of water and initially charged. This solution was heated with stirring to 50° C., and 20.4 g of 2,5-dichloroindan-1-one, dissolved in 100 ml of dimethylformamide, were then added dropwise over a period of 60 minutes. After the addition had ended, stirring was continued at 50° C. for 1 hour. The mixture was then allowed to cool to room temperature and the solvent was stripped off using a rotary evaporator. The resulting crystal slurry was mixed with 200 ml of water and acidified to pH 4.5 using 10% by weight strength aqueous hydrochloric acid. The precipitated solid was filtered off with suction, washed with water, recrystallized from toluene and dried in a vacuum drying cabinet. This gave 18.5 g of 2-cyano-5-chloroindan-1-one (yield: 97% of theory).

Workup

  1. additioninitially charged
  2. temperatureThis solution was heated
  3. additionwere then added dropwise over a period of 60 minutes
  4. additionAfter the addition
  5. stirringstirring
  6. temperatureto cool to room temperature
  7. customa rotary evaporator
  8. additionThe resulting crystal slurry was mixed with 200 ml of water
  9. filtrationThe precipitated solid was filtered off with suction
  10. washwashed with water
  11. customrecrystallized from toluene
  12. customdried in a vacuum
  13. customdrying cabinet

Sources & evidence

ORD record
ord-d79aac8f887444faae6ad4c84da97533
Source dataset
uspto-grants-2002_03
Patent number
US06355827B1

Reaction notes

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