Dimethylformamide → HCID 68154167, Verbindung

HRID 341100

Reaktionsgleichung

Reaktionsgleichung von HRID 341100
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][N+:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](Cl)=[C:11]([C:20]([O:22]CC)=O)[CH:10]=2)=[N:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Cl.[CH3:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[NH:39][NH2:40].CN(C)C=O>O.COCCOC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][N:9]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[C:12]3=[N:40][N:39]([C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=4[CH3:32])[C:20](=[O:22])[C:11]3=[CH:10]2)=[N:6][CH:7]=1

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 71554o-Tolylhydrazinium(1+) chlorideHCID 68153930HCID 68153930, Verbindung

Produkt 1

HCID 68154167HCID 68154167, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

1-[(5-Bromopyridin-2-yl)methyl]-4-chloro-3-(ethoxycarbonyl)quinolinium salt (1.55 g, 3.51 mmol), potassium carbonate (2.63 g, 19.1 mmol, 5.4 equiv), and (2-methylphenyl)hydrazine hydrochloride (1.33 g, 8.38 mmol, 2.4 equiv) were combined in a mixture (1:1) of N,N-dimethylformamide:1,2-dimethoxyethane (25 mL) and placed into an oil bath preheated at 80° C. for 3 hours. The mixture was cooled to ambient temperature, poured into water (100 mL) and extracted with dichloromethane (2×100 mL). The combined organic extracts were dried with sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel gradient chromatography (100:0 to 90:10; dichloromethane:methanol), providing the titled compound as a yellow solid: 1H-NMR (400 MHz, CD3OD) δ 8.97 (1H, s), 8.59 (1H, s), 8.33 (1H, d, J=7.8 Hz), 8.02-8.00 (1H, m), 7.78 (1H, d, J=9.0 Hz), 7.66-7.56 (2H, m), 7.48-7.37 (5H, m), 5.85 (2H, s), 2.28 (3H, s), ppm; low resolution mass spectrometry (ES+) m/z 446.8 [(M+H)+; calculated for C23H17BrN4O: 446.3].

Aufarbeitung

  1. extractionextracted with dichloromethane (2×100 mL)
  2. dry with materialThe combined organic extracts were dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel gradient chromatography (100:0 to 90:10; dichloromethane:methanol)

Quellen und Nachweise

ORD-Eintrag
ord-873757eabe91491aab7c8f0885940f3c
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895580B2

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