Dimethylformamide → 1H-Indole-6-carboxamide, N-(cyclopentylmethyl)-3-formyl-

Reaktionsgleichung

P(Cl)(Cl)(Cl)=O.[CH:6]1([CH2:11][NH:12][C:13]([C:15]2[CH:23]=[C:22]3[C:18]([CH:19]=[CH:20][NH:21]3)=[CH:17][CH:16]=2)=[O:14])[CH2:10][CH2:9][CH2:8][CH2:7]1.[OH-].[Na+].CN(C)[CH:28]=[O:29]>>[CH:6]1([CH2:11][NH:12][C:13]([C:15]2[CH:23]=[C:22]3[C:18]([C:19]([CH:28]=[O:29])=[CH:20][NH:21]3)=[CH:17][CH:16]=2)=[O:14])[CH2:10][CH2:9][CH2:8][CH2:7]1

Komponenten

Edukt 4

HCID 6228Dimethylformamide2×

HCID 14798Sodium Hydroxide

HCID 24813Phosphorus oxychloride

HCID 149485056-(N-cyclopentylmethylcarbamoyl)indole

Produkt 1

HCID 99932821H-Indole-6-carboxamide, N-(cyclopentylmethyl)-3-formyl-Ausbeute 60 %

Versuchsvorschrift

N,N-Dimethylformamide (DMF)(20 ml) was cooled to 0° under an atmosphere of nitrogen and treated cautiously with phosphorus oxychloride (6.6 ml). This solution was stirred at 0° for 15 minutes, warmed to room temperature, and treated with a solution of 6-(N-cyclopentylmethylcarbamoyl)indole (14.3 g) in DMF (100 ml). The yellow mixture was stirred for 2 hours and then brought to pH 14 by the addition of ice and 20% (w/v) aqueous sodium hydroxide. The mixture was heated to reflux for 5 minutes and allowed to cool. The precipitate which formed was collected by filtration and triturated with ether to give 6-(N-cyclopentylmethylcarbamoyl)-3-formylindole (9.6 g, 60%) as a tan powder; mp 224°-225°.