Pyridine → Phenyl isoquinolin-4-ylcarbamate

HRID 571989

Reaktionsgleichung

Reaktionsgleichung von HRID 571989
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([NH2:11])=[CH:3][N:2]=1.N1C=CC=CC=1.Cl[C:19]([O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:20]>C(#N)C.O>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([NH:11][C:19](=[O:20])[O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:3][N:2]=1

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 902374-Aminoisoquinoline

Produkt 1

HCID 58442686Phenyl isoquinolin-4-ylcarbamateAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Isoquinolin-4-amine (296 mg, 2.05 mmol) was dissolved in acetonitrile. To the reaction mixture was added pyridine (0.20 mL, 2.46 mmol) and phenyl chloroformate (0.27 mL, 2.15 mmol), respectively and stirred at room temperature for 1 h. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure. The crude was purified by column chromatography to give phenyl isoquinolin-4-ylcarbamate (318 mg, 59%).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. concentrationThe organic layer was concentrated under reduced pressure
  3. customThe crude was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-115e81effb614df49d9fdd22c812890e
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029378B2

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