Pyridine → 4-Bromo-1-phenylisoquinoline

HRID 652726

Reaktionsgleichung

Reaktionsgleichung von HRID 652726
[C:1]1([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:17]Br.N1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:17][C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:8][CH:9]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 24408BromineHCID 1378821-Phenylisoquinoline

Produkt 1

HCID 133022834-Bromo-1-phenylisoquinolineAusbeute 41,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel2×

Versuchsvorschrift

20.5 g of 1-phenylisoquinoline are dissolved in 100 ml of carbon tetrachloride, and 16 g of bromine are added at room temperature. The temperature is raised slowly and the mixture is kept under reflux for 1 hour. 7.9 g of pyridine in 10 ml of carbon tetrachloride are added dropwise to the boiling reaction mixture in the course of 2 hours, and the mixture is then heated at reflux temperature for a further 18 hours. The reaction solution is decanted off from the resinous precipitate and is concentrated, and the residue is crystallized from diisopropyl ether. 11.7 g of 4-bromo-1-phenylisoquinoline of melting point 123°-125° C. are obtained. 0.7 g of 4-bromo-1-phenylisoquinoline, 0.45 g of copper cyanide and 10 ml of dimethylformamide are heated at 160° C. for 6 hours. The reaction solution is decanted off, diluted with methylene chloride and washed with water. 0.75 g of crude product are isolated from the methylene chloride phase, and 0.2 g of 4-cyano-1-phenylisoquinoline of melting point 138°-140° is obtained from this crude product by column chromatography over silica gel using a 98:2 mixture of chloroform and ethyl acetate. 0.2 g of 4-cyano-1-phenylisoquinoline is heated with 10 ml of 20% strength sodium hydroxide solution at 100° C. for 4 hours. The solution is cooled and acidified with acetic acid. The precipitate is filtered off and dried. 0.18 g of 1-phenylisoquinoline-4-carboxylic acid of melting point 215°-217° is isolated.

Aufarbeitung

  1. temperatureThe temperature is raised slowly
  2. temperatureunder reflux for 1 hour
  3. temperaturethe mixture is then heated
  4. temperatureat reflux temperature for a further 18 hours
  5. customThe reaction solution is decanted off from the resinous precipitate
  6. concentrationis concentrated
  7. customthe residue is crystallized from diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-cd621d367bda48ea825bbc8a665d5859
Quelldatensatz
uspto-grants-1987_06
Patentnummer
US04673682

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