HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 12263Erstellt: 24. Oktober 2026
Triethylamine → 10h-Indolo[3,2-b]quinoline-11-carboxylic acid(2-dimethylamino-propyl)amide
https://huagongshe.com/de/reaction/12263
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
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| Edukt | Triethylamine | HCID 8471 | — |
| Edukt | 2-Amino-1-dimethylaminopropane | HCID 99027 | — |
| Edukt | 10H-Indolo[3,2-b]quinoline-11-carboxylic acid | HCID 10106757 | — |
| Lösungsmittel | Dichloromethane | HCID 6344 | — |
| Lösungsmittel | Thionyl Chloride | HCID 24386 | — |
| Produkt | 10h-Indolo[3,2-b]quinoline-11-carboxylic acid(2-dimethylamino-propyl)amide | HCID 11450844 | 31% |
Reaktionsschritte
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).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US07728000B2 |
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| Quelldatensatz | uspto-grants-2010_06 |
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| ORD ID | ord-35de871dc825411f82857dabd9c55ffb |
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| Quellennotiz | uspto-grants-2010_06 |
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