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

HRID 12263
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 12263
[CH:1]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:2]=1[C:3]([C:18]([OH:20])=O)=[C:4]1[NH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:5]1=[N:6]2.[CH3:21][N:22]([CH3:27])[CH2:23][CH:24]([NH2:26])C.[CH2:28](N(CC)CC)C>O=S(Cl)Cl.C(Cl)Cl>[CH3:21][N:22]([CH3:27])[CH:23]([CH3:28])[CH2:24][NH:26][C:18]([C:3]1[C:2]2[C:7](=[CH:8][CH:9]=[CH:10][CH:1]=2)[N:6]=[C:5]2[C:11]3[C:16]([NH:17][C:4]=12)=[CH:15][CH:14]=[CH:13][CH:12]=3)=[O:20]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 990272-Amino-1-dimethylaminopropaneHCID 1010675710H-Indolo[3,2-b]quinoline-11-carboxylic acid

Produkt 1

HCID 1145084410h-Indolo[3,2-b]quinoline-11-carboxylic acid(2-dimethylamino-propyl)amideAusbeute 31 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel
HCID 24386Thionyl ChlorideLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  1. customAfter 6 hours a clear solution was obtained
  2. customall volatiles were removed in vacuo
  3. washThe organic phase was washed (NaHCO3, brine)
  4. dry with materialdried (MgSO4)
  5. customRemoval of the solvent and purification by chromatography on alumina (CH2Cl2/MeOH, 90:10)

Quellen und Nachweise

ORD-Eintrag
ord-35de871dc825411f82857dabd9c55ffb
Quelldatensatz
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07728000B2

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