Chloroform → HCID 14853009, compound

HRID 845059Notes

Reaction equation

HRID 845059 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH:6]([CH3:12])[CH2:5]2.C(Cl)(Cl)Cl.[N:17]1C2C(=CC=CC=2)C=C[CH:18]=1>>[C:18]([C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH:6]([CH3:12])[CH2:5]2)#[N:17]

Participants

4

Reactant 3

HCID 6212ChloroformHCID 7047QuinolineHCID 148530085-Bromo-2-methyl-2,3-dihydro-1H-inden-1-one

Product 1

HCID 14853009HCID 14853009, compound

Procedure

5-Bromo-2-methyl-1-indanone (2.0 g) and cuprous cyanide (4.0 g) in quinoline (50 ml ) were stirred at 200° for 2 hours. The mixture was cooled, treated with chloroform (100 ml ) and filtered to remove copper salts. The filtrate was then washed with 6N hydrochloric acid (3×100 ml ) and evaporated to give the crude product as a brown gum. Crystallisation from ethanol-water gave 5-cyano-2-methyl-1-indanone (1.46 g, m.p. 90°-1°).

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. customto remove copper salts
  4. washThe filtrate was then washed with 6N hydrochloric acid (3×100 ml )
  5. customevaporated
  6. customto give the crude product as a brown gum
  7. customCrystallisation from ethanol-water

Sources & evidence

ORD record
ord-39cc4c9c75834ca3a024e169746733c3
Source dataset
uspto-grants-1988_07
Patent number
US04755511

Reaction notes

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