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

HRID 1156900Notes

Reaction equation

HRID 1156900 reaction equation
[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

Participants

7

Reactant 4

HCID 3301EthylenediamineHCID 12679HexamethylphosphoramideHCID 12851841HCID 12851841, compoundHCID 178418260HCID 178418260, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-b9aea8f511454988b5a7239d2b7982f9
Source dataset
uspto-grants-1982_06
Patent number
US04337256

Reaction notes

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