Pyridine → HCID 53374093, Verbindung

HRID 40770Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 40770
[NH2:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[CH:5]=[CH:4][C:3]=1[NH2:18].N1C=[CH:23][CH:22]=[CH:21][CH:20]=1.[C:25]1([CH3:34])[CH:30]=[CH:29][C:28]([C:31](Cl)=[O:32])=[CH:27][CH:26]=1.C(OCC)(=O)C.[O:41]1[CH2:45][CH2:44][CH2:43][CH2:42]1>CCO.CCCCCC>[CH3:34][C:25]1[CH:30]=[CH:29][C:28]([C:31]([NH:1][C:2]2[C:15]3[C:14](=[O:16])[C:13]4[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=4)[C:7](=[O:17])[C:6]=3[CH:5]=[CH:4][C:3]=2[NH:18][C:45](=[O:41])[C:44]2[CH:20]=[CH:21][C:22]([CH3:23])=[CH:42][CH:43]=2)=[O:32])=[CH:27][CH:26]=1

Komponenten

8

Edukt 5

HCID 1049PyridineHCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 134054-Methylbenzoyl ChlorideHCID 156521,2-Diaminoanthraquinone

Produkt 1

HCID 53374093HCID 53374093, VerbindungAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

1,2-diaminoanthraquinone (0.92 g, 4 mmole) was dissolved in anhydrous tetrahydrofuran (30 ml). To the solution, pyridine (0.5 ml), and 4-toluoyl chloride (1.6 ml, 12 mmole) were added successively at room temperature and the mixture was stirred for 5 to 10 minutes. Then, the mixture was stirred within a mini-reactor in an oil bath at temperature of 120-130° C. for 3 hours. After the completion of the reaction, the mixture was filtered, and the filtrate was concentrated by reduced pressure concentrator (such as Vacuum Evaporator). The residue was extracted with ethyl acetate for several times. The extract was dried on magnesium sulfate, and concentrated under reduced pressure. The crude product was washed with ethyl acetate/hexane. Finally, the crude product was recrystallized in hot ethanol to obtain a drab compound CC-04. Mol. Wt.: 474.5067 (C30H22N2O4); Rf: 0.51 (ethyl acetate:n-hexane=1:2); Yield: 62%; Mp.: 227-229° C. (EtOH); HRMS (EI) m/z: calcd [M]+, 474.1580 (C30H22N2O4+). Found, 474.1572. 1H-NMR (300 MHz, DMSO-d6) δ (ppm): 2.36 (s, 3H, —CH3), 2.42 (s, 3H, —CH3), 7.33 (d, J=8.4 Hz, 2H, Ar—H), 7.42 (d, J=8.4 Hz, 2H, Ar—H), 7.79 (d, J=8.1 Hz, 2H, Ar—H), 7.90-7.93 (m, 2H, Ar—H), 8.01 (d, J=8.1 Hz, 1H, Ar—H), 8.13-8.16 (m, 1H, Ar—H), 8.18-8.20 (m, 1H, Ar—H), 8.42 (d, J=8.7 Hz, 1H, Ar—H), 10.06 (s, 1H, Ar—NH—), 10.90 (s, 1H, Ar—NH—); 13C-NMR (300 MHz, DMSO-d6) δ (ppm): 20.37, 20.48, 125.02, 125.90, 126.61, 126.90, 127.45, 128.88, 128.92, 129.28, 129.70, 129.99, 130.39, 130.57, 131.79, 133.85, 134.00, 134.14, 138.94, 142.12, 142.20, 164.50 (NCO), 165.85 (NCO), 181.21 (CO), 183.84 (CO).

Aufarbeitung

  1. stirringThen, the mixture was stirred within a mini-reactor in an oil bath at temperature of 120-130° C. for 3 hours
  2. customAfter the completion of the reaction
  3. filtrationthe mixture was filtered
  4. concentrationthe filtrate was concentrated by reduced pressure concentrator (such as Vacuum Evaporator)
  5. extractionThe residue was extracted with ethyl acetate for several times
  6. customThe extract was dried on magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. washThe crude product was washed with ethyl acetate/hexane
  9. customFinally, the crude product was recrystallized in hot ethanol
  10. customto obtain a drab compound CC-04

Quellen und Nachweise

ORD-Eintrag
ord-3f036c9b045b4b59b7143bf69dd4d26d
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530465B2

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