Phosphorus oxychloride → 6-Bromo-1-chloro-isoquinoline

HRID 1067232Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1067232
P(Cl)(Cl)([Cl:3])=O.[Br:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[CH:13]=[N+:12]([O-])[CH:11]=[CH:10]2>C(Cl)Cl>[Br:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13]([Cl:3])=[N:12][CH:11]=[CH:10]2

Komponenten

4

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 222501786-Bromoisoquinoline 2-oxide

Produkt 1

HCID 222502446-Bromo-1-chloro-isoquinolineAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Phosphorus oxychloride (0.60 mL, 6.44 mmol) was added in one portion to a stirred solution of 6-bromoisoquinoline N-oxide (409 mg, 1.83 mmol) in CH2Cl2 (10 mL) and the mixture was heated at reflux for 6 hours. Excess solvents were evaporated in vacuo, the residue suspended in water (10 mL) and basified with 0.880 ammonia. This mixture was extracted with CH2Cl2 (2×25 mL) and the combined organics were dried over MgSO4 and evaporated in vacuo to leave the crude product. Purification by column chromatography upon silica gel using hexanes-EtOAc (90:10) as eluant gave 6-bromo-1-chloroisoquinoline (215 mg, 0.86 mmol) as a cream-coloured solid.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 6 hours
  3. customExcess solvents were evaporated in vacuo
  4. extractionThis mixture was extracted with CH2Cl2 (2×25 mL)
  5. dry with materialthe combined organics were dried over MgSO4
  6. customevaporated in vacuo
  7. customto leave the crude product
  8. customPurification by column chromatography upon silica gel

Quellen und Nachweise

ORD-Eintrag
ord-eea1920dc6374e42938df1f81909520d
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06248738B1

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