Hexanal → ethyl 3-butyl-1H-indole-5-carboxylate

HRID 349001

Reaktionsgleichung

Reaktionsgleichung von HRID 349001
Cl.[NH:2]([C:4]1[CH:14]=[CH:13][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][CH:5]=1)N.[CH:15](=O)[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>C(O)C.O>[CH2:17]([C:16]1[C:14]2[C:4](=[CH:5][CH:6]=[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:13]=2)[NH:2][CH:15]=1)[CH2:18][CH2:19][CH3:20]

Komponenten

4

Edukt 2

HCID 6184HexanalHCID 12414202Ethyl 4-hydrazinylbenzoate hydrochloride

Produkt 1

HCID 21086100ethyl 3-butyl-1H-indole-5-carboxylateAusbeute 7,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 19096565Water ethanolLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a mixture of ethyl 4-hydrazinobenzoate hydrochloride (10 gm) in ethanol: water (5:1 100 mL) was added hexanal (4.62 gm). The mixture was refluxed at 100° C. for 3 h. The solvents were removed and toluene (100 mL) and p-toluene sulfonic acid (0.1 g) were added. The mixture was refluxed at 120° C. for 18 h, cooled to room temperature and concentrated under reduced pressure. Column chromatography on silica gel (100 mL) using 90:9:1 (hexanes: methylene chloride: ethyl acetate) as eluent to give 0.8 g of the title compound: 1H NMR (CDCl3) δ 0.957, 1.44, 1.72, 2.78, 4.40, 7.02, 7.34, 7.90, 8.13, 8.38.

Aufarbeitung

  1. customThe solvents were removed
  2. additiontoluene (100 mL) and p-toluene sulfonic acid (0.1 g) were added
  3. temperatureThe mixture was refluxed at 120° C. for 18 h
  4. temperaturecooled to room temperature
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-437a19f7883c40ad8caaf32ba62939f7
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07176242B2

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