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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°).

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