Hydrochloric Acid → 4,6-Dichloro-1H-indole

HRID 375214

Reaktionsgleichung

Reaktionsgleichung von HRID 375214
[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5](C(O)=O)[NH:6]2.Cl>N1C2C(=CC=CC=2)C=CC=1.[Cu]>[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 1279884,6-Dichloro-1H-indole-2-carboxylic acid

Produkt 1

HCID 144196244,6-Dichloro-1H-indoleAusbeute 93,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23978CopperKatalysatorHCID 7047QuinolineLösungsmittel

Versuchsvorschrift

Dissolve 4,6-dichloro-indole-2-carboxylic acid (1.0 g, 4.35 mmol) in quinoline (25 mL). Add copper powder (100 mg) and heat to 220° C. for 3 hours. Pour the resulting black solution into cold concentrated hydrochloric acid (300 mL) and extract into ethyl ether (500 mL). Filter, wash with 1M hydrochloric acid (2×200 mL), water (100 mL) and dry (MgSO4). Evaporate the solvent in vacuo to give a brown oil (0.76 g). Purify by silica gel chromatography (17% ethyl acetate/hexane) to give the title compound as an amber oil (0.66 g, 81%).

Aufarbeitung

  1. extractionextract into ethyl ether (500 mL)
  2. filtrationFilter
  3. washwash with 1M hydrochloric acid (2×200 mL), water (100 mL)
  4. dry with materialdry (MgSO4)
  5. customEvaporate the solvent in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-00dc046f998448c5b40795963d8d69b8
Quelldatensatz
uspto-grants-1996_01
Patentnummer
US05484814

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