반응 #40541

반응 방정식

N,N-dimethylproylendiamine

triethylamine

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

→

desired compound

수율 31.0%

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

수율 31.0%

용매

CH2Cl2

SOCl2

반응 조건

후처리

1. 1
   기타After 6 hours a clear solution was obtained
2. 2
   기타all volatiles were removed in vacuo
3. 3
   세척The organic phase was washed (NaHCO3, brine)
4. 4
   건조dried (MgSO4)
5. 5
   기타Removal of the solvent and purification by chromatography on alumina (CH2Cl2/MeOH, 90:10)

실험 절차

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).

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