3,4-Dinitrophenol → 4-(3,4-dinitro-phenoxy)-1H-pyrrolo[2,3-b]pyridine

HRID 491650Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 491650
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][CH:9]=[CH:10][C:3]=12.[N+:11]([C:14]1[CH:15]=[C:16]([OH:23])[CH:17]=[CH:18][C:19]=1[N+:20]([O-:22])=[O:21])([O-:13])=[O:12]>[OH-].[Na+].C(Cl)Cl>[N+:11]([C:14]1[CH:15]=[C:16]([CH:17]=[CH:18][C:19]=1[N+:20]([O-:22])=[O:21])[O:23][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][CH:9]=[CH:10][C:3]=12)([O-:13])=[O:12]

Komponenten

5

Edukt 2

HCID 113483,4-DinitrophenolHCID 113894934-Chloro-1H-pyrrolo[2,3-b]pyridine

Produkt 1

HCID 177564904-(3,4-dinitro-phenoxy)-1H-pyrrolo[2,3-b]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A mixture of 4-chloro-1H-pyrrolo[2,3-b]pyridine (Step B, 1.0 g, 6.5 mmol) and 3,4-dinitrophenol (1.41 g, 7.6 mmol) was heated at 150° C. for 8 h. The resulting crude solid was dissolved in NaOH (12N) and CH2Cl2. The aqueous layer was extracted several times with CH2Cl2. The insoluble material was solubilized in acetone. The acetone solution was diluted with CH2Cl2 and washed with water. The combined CH2Cl2 layers were dried and concentrated under vacuum. The crude material was purified on silica gel using a CH2Cl2/EtOH gradient (100/0 to 90/10) to give 4-(3,4-dinitro-phenoxy)-1H-pyrrolo[2,3-b]pyridine.

Aufarbeitung

  1. extractionThe aqueous layer was extracted several times with CH2Cl2
  2. additionThe acetone solution was diluted with CH2Cl2
  3. washwashed with water
  4. dry with materialThe combined CH2Cl2 layers were dried
  5. concentrationconcentrated under vacuum
  6. customThe crude material was purified on silica gel using a CH2Cl2/EtOH gradient (100/0 to 90/10)

Quellen und Nachweise

ORD-Eintrag
ord-533a4370ceca401981bea474b48e0d52
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07531553B2

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