Nitromethane → 6-(2-Nitrovinyl)-1H-indole

HRID 351596

Reaktionsgleichung

Reaktionsgleichung von HRID 351596
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:10]=O)[CH:8]=2)[CH:3]=[CH:2]1.C([O-])(=O)C.[NH4+].[N+:17]([CH3:20])([O-:19])=[O:18]>>[N+:17]([CH:20]=[CH:10][C:7]1[CH:8]=[C:9]2[C:4]([CH:3]=[CH:2][NH:1]2)=[CH:5][CH:6]=1)([O-:19])=[O:18]

Komponenten

4

Edukt 3

HCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 27734351H-Indole-6-carboxaldehyde

Produkt 1

HCID 697441266-(2-Nitrovinyl)-1H-indoleAusbeute 91 %

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of indole-6-carboxaldehyde (2.8 g), nitromethane (30 mL) and ammonium acetate (0.560 g) was stirred at 100° C. for 30 minutes. The excess nitromethane was removed under reduced pressure and the residue washed with water, dissolved in ethyl acetate (500 mL), dried over sodium sulfate, filtered, and the filtrate concentrated under reduced pressure to a volume of about 50 mL. This solution was then diluted with petroleum ether and the resulting suspension filtered and dried to provide 3.3 g (91%) of the desired compound.

Aufarbeitung

  1. customThe excess nitromethane was removed under reduced pressure
  2. washthe residue washed with water
  3. dissolutiondissolved in ethyl acetate (500 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under reduced pressure to a volume of about 50 mL
  7. additionThis solution was then diluted with petroleum ether
  8. filtrationthe resulting suspension filtered
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-8b8c1767e2a74f4fbdaa4cba872d5f28
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06743785B2

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