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

HRID 2368763Notes

Reaction equation

HRID 2368763 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(OCC)(=O)C.[CH3:18][N:19](C)C=O>>[O:11]=[C:7]1[C:8]2[C:4](=[CH:3][C:2]([C:18]#[N:19])=[CH:10][CH:9]=2)[CH2:5][CH2:6]1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 5206955-Bromo-1-indanone

Product 1

HCID 3128961-oxo-2,3-dihydro-1H-indene-5-carbonitrileYield 50%

Conditions

Temperature
140 °C

Procedure

5-Bromo-2,3-dihydro-1H-inden-1-one (21.1 g, 100 mmol) and cupric cyanide (17.9 g, 200 mmol) were mixed in 200 ml of dimethylformamide and stirred overnight at 140° C. After the solution was cooled down to room temperature, 500 ml of ethyl acetate was added and the precipitate was removed by filteration using kieselguhr. The solid was rinsed with ethyl acetate for several times. The pooled filtrates were washed with 1 N hydrochloric acid twice and then with brine for 3 times, dried over anhydrous magnesium sulfate, filtered, and concentrated. The crude product was purified on silica gel, eluting with ethyl acetate/hexanes (1:2), to obtain 7.9 g of the desired compound (50% yield). MS (M+1)=158.05.

Workup

  1. temperatureAfter the solution was cooled down to room temperature
  2. customthe precipitate was removed by filteration
  3. washThe solid was rinsed with ethyl acetate for several times
  4. washThe pooled filtrates were washed with 1 N hydrochloric acid twice
  5. dry with materialwith brine for 3 times, dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified on silica gel
  9. washeluting with ethyl acetate/hexanes (1:2)

Sources & evidence

ORD record
ord-6ad8362a660443cbb827e75d53d95603
Source dataset
uspto-grants-2014_04
Patent number
US08703771B2

Reaction notes

Loading…