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

HRID 1156900Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1156900
[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

Komponenten

7

Edukt 4

HCID 3301EthylenediamineHCID 12679HexamethylphosphoramideHCID 12851841HCID 12851841, VerbindungHCID 178418260HCID 178418260, Verbindung

Produkt 1

HCID 128518421-(4-Methylphenyl)-5-cyanoisoquinolineAusbeute 77,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-b9aea8f511454988b5a7239d2b7982f9
Quelldatensatz
uspto-grants-1982_06
Patentnummer
US04337256

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