Pyridine → 6,7-dihydro-5H-dibenzo[a,c]cyclohepten-4-carbonitrile

HRID 1388821Notes

Reaction equation

HRID 1388821 reaction equation
Cl[C:2]1[C:7]2[CH2:8][CH2:9][CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1.[N:17]1C=CC=C[CH:18]=1>C(Cl)Cl>[CH:5]1[C:6]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[CH2:10][CH2:9][CH2:8][C:7]=2[C:2]([C:18]#[N:17])=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 1049PyridineHCID 132813394-chloro-6,7-dihydro-5H-dibenzo[a,c]cycloheptene

Product 1

HCID 132813406,7-dihydro-5H-dibenzo[a,c]cyclohepten-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under a dry nitrogen atmosphere a mixture of 4-chloro-6,7-dihydro-5H-dibenzo[a,c]cycloheptene (1.6 grams, 0.007 mole), cuprous cyanide (0.95 gram, 0.011 mole), and pyridine (0.8 gram, 0.01 mole) was stirred and heated at 195° for approximately 16 hours. The mixture was cooled, dissolved in methylene chloride (150 ml), and the resultant solution was washed with three 70 ml portions of concentrated ammonium hydroxide. The organic phase was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure to give a brown solid. Recrystallization from n-hexane gave 6,7-dihydro-5H-dibenzo[a,c]cycloheptene-4-carbonitrile (mp 109°-111°).

Workup

  1. temperatureheated at 195° for approximately 16 hours
  2. temperatureThe mixture was cooled
  3. washthe resultant solution was washed with three 70 ml portions of concentrated ammonium hydroxide
  4. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe filtrate was evaporated under reduced pressure
  7. customto give a brown solid
  8. customRecrystallization from n-hexane

Sources & evidence

ORD record
ord-c99280b163be47f5a1fe7fbeaafb2b9e
Source dataset
uspto-grants-1984_02
Patent number
US04433182

Reaction notes

Loading…