Hydrochloric Acid → 3-cyano-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one

HRID 1415170Notes

Reaction equation

HRID 1415170 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][CH2:10][C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[C:7](=[O:16])[C:6]=2[CH:17]=1.[Cu](C#N)[C:19]#[N:20].CN(C)C=O.Cl>[Fe](Cl)(Cl)Cl.O>[C:19]([C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][CH2:10][C:9]3[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=3[C:7](=[O:16])[C:6]=2[CH:17]=1)#[N:20]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 129093912-Bromo-5,6-dihydrodibenzo[3,1-[7]annulen-11-oneHCID 178418260HCID 178418260, compound

Product 1

HCID 130308153-cyano-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one

Reagents, catalysts & solvents 2

HCID 24380Iron chloride (FeCl3)CatalystHCID 962WaterSolvent

Procedure

7.2 g. of 3-bromo-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one, together with 2.7 g. of copper cyanide and 10 ml. of dimethylformamide, are heated to boiling under reflux conditions for 6 hours. The resulting hot solution is poured into a solution containing 10 g. of iron trichloride in 15 ml. of water and 3 ml. of concentrated hydrochloric acid, stirred at 70° C. for 20 minutes and extracted with toluene. The toluene extract is washed first with 3N hydrochloric acid and then with 3N caustic soda, dried over sodium sulfate and evaporated. The 3-cyano-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one which is obtained, is purified by adsorption on the 10-fold amount of Kieselgel (eluting agent: toluene); melting point 104°-106° C.

Workup

  1. additionThe resulting hot solution is poured into a solution
  2. additioncontaining 10 g
  3. extractionextracted with toluene
  4. extractionThe toluene extract
  5. washis washed first with 3N hydrochloric acid
  6. dry with materialwith 3N caustic soda, dried over sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-7a557b4c6c2548bd9da31b4d288b41d9
Source dataset
uspto-grants-1977_01
Patent number
US04003915

Reaction notes

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