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

HRID 1388821ノート

反応式

HRID 1388821 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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°).

後処理

  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

出典と根拠

ORDレコード
ord-c99280b163be47f5a1fe7fbeaafb2b9e
出典データセット
uspto-grants-1984_02
特許番号
US04433182

反応ノート

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