Toluene → N-[2-(ethylamino)ethyl]-5-nitro-1H-indole-2-carboxamide

HRID 23149

Reaktionsgleichung

Reaktionsgleichung von HRID 23149
C(O[C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([N+:15]([O-:17])=[O:16])=[CH:10][CH:9]=2)=[O:5])C.C1(C)C=CC=CC=1.CCOCC.[CH2:30]([NH:32][CH2:33][CH2:34][NH2:35])[CH3:31]>C(OCC)(=O)C>[CH2:30]([NH:32][CH2:33][CH2:34][NH:35][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([N+:15]([O-:17])=[O:16])=[CH:10][CH:9]=2)=[O:5])[CH3:31]

Komponenten

6

Edukt 4

HCID 1140TolueneHCID 3283Diethyl EtherHCID 66071N-EthylethylenediamineHCID 280312Ethyl 5-nitro-1H-indole-2-carboxylate

Produkt 1

HCID 85801380N-[2-(ethylamino)ethyl]-5-nitro-1H-indole-2-carboxamideAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A fine powder of 5-nitro-2-indolecarboxylic acid ethyl ester (0.8 g, 3.41 mmol) was suspended in 2 ml of N-ethylethylenediamine under argon and the reaction mixture was stood at 55° C. overnight. The mixture was co-evaporated with toluene to dryness. The brown solid obtained was dissolved in 6 ml of ethyl acetate and 40 ml of ether was added to precipitate the product. After centrifugation, the liquid was poured out and the solid was washed with 30 ml of ether and dried to give small brown crystals (0.77 g, 82%). ESI MS: 277.11 (M+H+), 299.09 (M+Na+). 1H NMR (DMSO-d6) δ8.67 (d, 1H), 8.04 (dd, 1H), 7.55 (d, 1H), 7.37 (s), 3.36 (m, 3H), 2.69 (q, 2H), 2.55 (q, 2H), 0.99 (t, 3H).

Aufarbeitung

  1. customThe brown solid obtained
  2. customto precipitate the product
  3. additionAfter centrifugation, the liquid was poured out
  4. washthe solid was washed with 30 ml of ether
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-40e663da5a7b4c6aa33aec3ec44db7c1
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06849713B2

Verknüpfte Notizen

Wird geladen…