Acetic Acid → 5-bromo-3-(pyridin-3-ylmethyl)-1H-indole

HRID 355984

Reaktionsgleichung

Reaktionsgleichung von HRID 355984
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][CH:9]=O)[CH:2]=1.Cl.[Br:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19]N)=[CH:15][CH:14]=1.C(O)(=O)C>C(O)C>[Br:12][C:13]1[CH:14]=[C:15]2[C:16](=[CH:17][CH:18]=1)[NH:19][CH:9]=[C:8]2[CH2:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 121574-Bromophenylhydrazine hydrochlorideHCID 111054123-(Pyridin-3-yl)propanal

Produkt 1

HCID 189408375-bromo-3-(pyridin-3-ylmethyl)-1H-indole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 3-pyridin-propionaldehyde (1 g; 0.0074 mol) and of 4-bromophenylhydrazin hydrochloride (1.8 g; 0.0074 mol) with acetic acid (4.44 ml) in absolute ethanol (50 ml) was refluxed for 3 hours. The reaction was then quenched with a saturated solution of aqueous sodium carbonate and the product was extracted with ethyl acetate. The organic extract was dried (MGSO4) and evaporated under vacuum. After purification by Flash Chromatography on silica gel using as eluent methylene chloride/methanol (98/2), the desired compound was obtained.

Aufarbeitung

  1. customThe reaction was then quenched with a saturated solution of aqueous sodium carbonate
  2. extractionthe product was extracted with ethyl acetate
  3. extractionThe organic extract
  4. customwas dried (MGSO4)
  5. customevaporated under vacuum
  6. customAfter purification by Flash Chromatography on silica gel using as eluent methylene chloride/methanol (98/2)

Quellen und Nachweise

ORD-Eintrag
ord-bfb74f571a174ea787722b430fdb89e4
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05834493

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