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

HRID 2164831노트

반응식

HRID 2164831 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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 give 6,7-dihydro-5H-dibenzo[a,c]cycloheptene-4-carbonitrile (mp 109°-111°).

후처리

  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

출처 및 근거

ORD 기록
ord-d59becd13e7d44939be4ffe511387dd5
출처 데이터셋
uspto-grants-1985_03
특허 번호
US04507317

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