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

HRID 236617

Reaktionsgleichung

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

Reaktionsbedingungen

Temperatur: 160 °C

Versuchsvorschrift

A mixture of 27.7 grams (0.1 mole) of 1,8-dichloroanthraquinone, 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. It was recrystallized from isopropanol to yield 29 grams (62%) of 1,8-bis[2-(p-hydroxyphenyl)ethylamino]anthraquinone as a red powder, m.p. 181°-182° C., vis (DMF), λmax 520 nm (ε12,000); ms 478 (M+); Calcd. 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

temperatureThe mixture was cooled to room temperature
filtrationthe product was collected by filtration
customIt was recrystallized from isopropanol

Quellen und Nachweise

ORD-Eintrag: ord-771a6ff03c994412a3b98da0e507c208
Quelldatensatz: uspto-grants-1987_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04645727

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