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

HRID 1589881Notes

Reaction equation

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

Participants

Conditions

Temperature: 160 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-bdfec3c3ab3c49ebb1065d51df61ff09
Source dataset: uspto-grants-1993_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05200290

Reaction notes

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