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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 12262Erstellt: 23. Oktober 2026

Triethylamine → 10H-indolo[3,2-b]quinoline-11-carboxylic acid (2-dimethylamino-ethyl)amide

https://huagongshe.com/de/reaction/12262

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktTriethylamineHCID 8471—
EduktN,N-DimethylethylenediamineHCID 66053—
Edukt10H-Indolo[3,2-b]quinoline-11-carboxylic acidHCID 10106757—
LösungsmittelDichloromethaneHCID 6344—
LösungsmittelThionyl ChlorideHCID 24386—
Produkt10H-indolo[3,2-b]quinoline-11-carboxylic acid (2-dimethylamino-ethyl)amideHCID 1147303461%

Reaktionsschritte

10H-indolo[3,2-b]quinoline-11-carboxylic acid (0.5 g, 1.9 mmol) was dissolved in 20 ml of refluxing SOCl2, After 6 hours a clear solution was obtained, and all volatiles were removed in vacuo. The crude acid chloride was suspended in 10 ml of CH2Cl2. A solution of N,N-dimethylethylendiamine (0.2 mL, 2.26 mmol) and triethylamine (2.2 ml) in 10 ml of CH2Cl2 was added at room temperature, and the mixture was stirred for 14 hours. The organic phase was washed (NaHCO3, brine) and dried (MgSO4). Removal of the solvent and purification by chromatography on alumina (CH2Cl2/MeOH, 90:10) yielded the desired compound (0.38 g, 61%) as a solid. m. p. 175-176° C. 1H-NMR [MeOD, _, ppm]: 8.16 (d, J=7.8 Hz, 1H), 7.92 (m, 2H), 7.35-7.20 (m, 3H), 7.04 (m, 2H), 3.62 (m, 2H, CH2NO), 2.55 (m, 2H, CH2N(CH3)2), 2.29 (s, 6H, N(CH3)j. MS (EI, m/z) 277 (M++1).

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS07728000B2
Quelldatensatzuspto-grants-2010_06
ORD IDord-5ef6c1c4b096459d8233747f623d138d
Quellennotizuspto-grants-2010_06