Phosphorus oxychloride → 7-Bromo-1-Chloroisoquinoline

HRID 551273Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 551273
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][NH:8][C:9]2=O)=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:15])=O.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[C:9]2[Cl:15])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 112761337-Bromoisoquinolin-1-ol

Produkt 1

HCID 65020247-Bromo-1-ChloroisoquinolineAusbeute 61,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

7-Bromo-2H-isoquinolin-1-one (3.0 g, 13.4 mmol), phosphorus oxychloride (8.22 g, 53.6 mmol), and chloroform (25 mL) combined in a sealed tube and heated with stirring at 100° C. for 4 hours. Cooled to ˜60° C., poured into ice water (100 mL), neutralized carefully with saturated aqueous sodium hydrogencarbonate, extracted into methylene chloride and dried over magnesium sulfate. Flash column chromatography on silica gel gave the product as a pale cream solid (2.01 g, 8.3 mmol). 1H NMR (CDCl3) δ 8.51 (d, 1H), 8.30 (d, 1H), 7.82 (dd, 1H), 7.72 (d, 1H), 7.57 (dd, 1H). ESI MS (M+1)+: 242, 244, 246 (Br, Cl).

Aufarbeitung

  1. temperatureheated
  2. temperatureCooled to ˜60° C.
  3. extractionextracted into methylene chloride
  4. dry with materialdried over magnesium sulfate

Quellen und Nachweise

ORD-Eintrag
ord-2264de8a5346429cb01dc3bcb5f89043
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07947684B2

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