Реакция #40540

Уравнение реакции

N,N-dimethylethylendiamine

triethylamine

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

→

desired compound

Выход 61.0%

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

Выход 61.0%

Растворители

CH2Cl2

SOCl2

Условия реакции

Обработка

1. 1
   Другоеwas obtained
2. 2
   Другоеall volatiles were removed in vacuo
3. 3
   ПромывкаThe organic phase was washed (NaHCO3, brine)
4. 4
   Сушкаdried (MgSO4)
5. 5
   ДругоеRemoval of the solvent and purification by chromatography on alumina (CH2Cl2/MeOH, 90:10)

Методика

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).

Источник