Tyramine → 1,8-Bis{[2-(4-hydroxyphenyl)ethyl]amino}anthracene-9,10-dione

HRID 1589881Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1589881
Cl[C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][C:12]=3Cl)[C:7](=[O:18])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[NH2:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1>ClC1C=CC=CC=1Cl>[OH:28][C:25]1[CH:26]=[CH:27][C:22]([CH2:21][CH2:20][NH:19][C:2]2[C:15]3[C:14](=[O:16])[C:13]4[C:8](=[CH:9][CH:10]=[CH:11][C:12]=4[NH:19][CH2:20][CH2:21][C:22]4[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=4)[C:7](=[O:18])[C:6]=3[CH:5]=[CH:4][CH:3]=2)=[CH:23][CH:24]=1

Komponenten

4

Edukt 2

HCID 5610TyramineHCID 67081,8-Dichloroanthraquinone

Produkt 1

HCID 220980051,8-Bis{[2-(4-hydroxyphenyl)ethyl]amino}anthracene-9,10-dioneAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 72391,2-DichlorobenzeneLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

A mixture of 27.7 grams (0.1 mole) of 1,8-dichloroanthraquinone, and 30 grams (0.22 mole) of p-(2-aminoethyl)phenol in 200 milliliters of o-dichlorobenzene was heated to 160° C. for 18 hours. The mixture was cooled to room temperature, and the product was collected by filtration. Thereafter, the aforementioned product was recrystallized from isopropanol to yield 29 grams (62 percent) of 1,8-bis[2-(p-hydroxyphenyl)ethylamino]anthraquinone as a red powder, m.p. 181° to 182° C.; vis (DMF), λmax 520 nm (ε 12,000); ms 478 (M+); Analysis Calculated for C30H26N2O4 : C, 75.29; H, 5.48; N, 5.86; O. 13.38. Found: C, 74.94; H, 5.30; N, 5.63; O, 13.17.

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationthe product was collected by filtration
  3. customThereafter, the aforementioned product was recrystallized from isopropanol

Quellen und Nachweise

ORD-Eintrag
ord-bdfec3c3ab3c49ebb1065d51df61ff09
Quelldatensatz
uspto-grants-1993_04
Patentnummer
US05200290

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