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

HRID 1388821Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1388821
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

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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°).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-c99280b163be47f5a1fe7fbeaafb2b9e
Quelldatensatz
uspto-grants-1984_02
Patentnummer
US04433182

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