Reaktion #40540

Reaktionsgleichung

N,N-dimethylethylendiamine

triethylamine

10H-indolo[3,2-b]quinoline-11-carboxylic acid

→

desired compound

Ausbeute 61.0%

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

Ausbeute 61.0%

Lösungsmittel

CH2Cl2

SOCl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas obtained
2. 2
   Sonstigeall volatiles were removed in vacuo
3. 3
   WaschenThe organic phase was washed (NaHCO3, brine)
4. 4
   Trocknendried (MgSO4)
5. 5
   SonstigeRemoval of the solvent and purification by chromatography on alumina (CH2Cl2/MeOH, 90:10)

Vorschrift

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).

Quelle