Reaktion #40541

Reaktionsgleichung

N,N-dimethylproylendiamine

triethylamine

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

→

desired compound

Ausbeute 31.0%

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

Ausbeute 31.0%

Lösungsmittel

CH2Cl2

SOCl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAfter 6 hours a clear solution was 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 (0.2 g, 0.76 mmol) was dissolved in 8 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-dimethylproylendiamine (0.1 mL, 0.97 mmol) and triethylamine (1 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 (80 mg, 31%) as a solid. m. p. 188-189° 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)2), 1.88 (m, 2H, CHO. MS (EI, m/z) 347 (M++1).

Quelle