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

HRID 1156900노트

반응식

HRID 1156900 반응식
[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

참가 물질

7

반응물 4

HCID 3301EthylenediamineHCID 12679HexamethylphosphoramideHCID 12851841HCID 12851841, 화합물HCID 178418260HCID 178418260, 화합물

생성물 1

HCID 128518421-(4-Methylphenyl)-5-cyanoisoquinoline수율 77.4%

시약·촉매·용매 2

HCID 241Benzene용매HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b9aea8f511454988b5a7239d2b7982f9
출처 데이터셋
uspto-grants-1982_06
특허 번호
US04337256

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