Ethylenediamine → 1-(4-Methylphenyl)-5-cyanoisoquinoline

HRID 1156900ノート

反応式

HRID 1156900 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[C:13](Cl)[CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[Cu](C#N)[C:20]#[N:21].CN(P(N(C)C)(N(C)C)=O)C.C(N)CN>C1C=CC=CC=1.O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[C:13]([C:20]#[N:21])[CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 3301EthylenediamineHCID 12679HexamethylphosphoramideHCID 12851841HCID 12851841、化合物HCID 178418260HCID 178418260、化合物

生成物 1

HCID 128518421-(4-Methylphenyl)-5-cyanoisoquinoline収率 77.4%

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 962Water溶媒

実験手順

A mixture of 22 g of 1-(4-methylphenyl)-5-chloroisoquinoline, 74.4 g of copper cyanide and 420 ml of hexamethylphosphotriamide was heated overnight under reflux. After the reaction, the reaction mixture was poured into a mixture of ethylenediamine, water and benzene, and stirred for 30 minutes. The mixture was then filtered through Celite. The benzene layer as filtrate was washed in water, and dried, followed by distilling off the solvent. The residue was recrystallized from ether to afford 16.4 g of 1-(4-methylphenyl)-5-cyanoisoquinoline as colorless needles having a melting point of 131.8° to 132.4° C.

後処理

  1. temperaturewas heated overnight
  2. temperatureunder reflux
  3. customAfter the reaction
  4. filtrationThe mixture was then filtered through Celite
  5. washThe benzene layer as filtrate was washed in water
  6. customdried
  7. distillationby distilling off the solvent
  8. customThe residue was recrystallized from ether

出典と根拠

ORDレコード
ord-b9aea8f511454988b5a7239d2b7982f9
出典データセット
uspto-grants-1982_06
特許番号
US04337256

反応ノート

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