Potassium Cyanide → 5,6-Dimethoxy-1-oxo-2,3-dihydro-1H-indene-2-carbonitrile

HRID 247015Notes

Reaction equation

HRID 247015 reaction equation
Br[CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][C:6]([O:13][CH3:14])=[C:7]([O:11][CH3:12])[CH:8]=2)[C:3]1=[O:15].[C-:16]#[N:17].[K+]>C(O)C.O>[C:16]([CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][C:6]([O:13][CH3:14])=[C:7]([O:11][CH3:12])[CH:8]=2)[C:3]1=[O:15])#[N:17]

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 109236312-Bromo-5,6-dimethoxy-indan-1-one

Product 1

HCID 201611865,6-Dimethoxy-1-oxo-2,3-dihydro-1H-indene-2-carbonitrileYield 44.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2-Bromo-5,6-dimethoxy-indan-1-one (69.1 g) was suspended in ethanol (1,200 ml) and added to a solution of potassium cyanide (70.4 g) in water (2,200 ml). The reaction mixture was heated at reflux for 1 hour and then the ethanol was distilled off. The dark solution was cooled, stirred and carefully neutralised with hydrochloric acid (5M, 120 ml) in a well ventilated hood. The organic extracts were combined, washed with brine, dried over magnesium sulphate, filtered, then concentrated to low volume under reduced pressure. The residual liquid was filtered through a column of coarse silica (0.2-0.5 mm, Merck, 300 g) and the column was eluted with dichloromethane. The appropriate fractions were combined and evaporated to dryness to give 2-Cyano-5,6-dimethoxy-indan-1-one (24.6 g). A portion crystallised from dichloromethane: ether; m.p. 177°-179° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 1 hour
  3. distillationthe ethanol was distilled off
  4. temperatureThe dark solution was cooled
  5. washwashed with brine
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated to low volume under reduced pressure
  9. filtrationThe residual liquid was filtered through a column of coarse silica (0.2-0.5 mm, Merck, 300 g)
  10. washthe column was eluted with dichloromethane
  11. customevaporated to dryness

Sources & evidence

ORD record
ord-11ece82495d24af4b251a3f6e7188615
Source dataset
uspto-grants-1987_11
Patent number
US04705782

Reaction notes

Loading…