Water → 1,4-Bis[2-(4-hydroxyphenyl)ethylamino]anthracene-9,10-dione

HRID 236618Notes

Reaction equation

HRID 236618 reaction equation
[CH2:1]1[C:15](=O)[C:14]2[C:5](=[C:6]([OH:18])[C:7]3[C:12]([C:13]=2[OH:17])=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:3](=O)[CH2:2]1.[NH2:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1.[OH2:29]>N1C=CC=CC=1>[OH:28][C:25]1[CH:26]=[CH:27][C:22]([CH2:21][CH2:20][NH:19][C:15]2[C:14]3[C:13](=[O:17])[C:12]4[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=4)[C:6](=[O:18])[C:5]=3[C:3]([NH:19][CH2:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([OH:29])=[CH:24][CH:23]=3)=[CH:2][CH:1]=2)=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 962WaterHCID 5610TyramineHCID 872111,4-Anthracenedione, 2,3-dihydro-9,10-dihydroxy-

Product 1

HCID 28172421,4-Bis[2-(4-hydroxyphenyl)ethylamino]anthracene-9,10-dioneYield 60%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 21 grams (0.09 mole) of leucoquinizarine, 30 grams (0.22 mole) of p-(2-aminoethyl)phenol in 150 milliliters of pyridine was refluxed for 12 hours. The mixture was cooled to room temperature and poured into 2 liters of water. Thereafter, the product was filtered, washed with water, and recrystillized from acetic acid to yield 26 grams, (60%) of 1,4-bis[2-(p-hydroxyphenyl)ethylamino]anthraquinone as a blue powder, m.p. 240°-242° C.; vis (DMF), λmax 644 nm (ε16,600); 598 nm (ε14,100); ms 478 (M+); Calcd. for C30H26N2O4 : C, 75.29; H, 5.48; N, 5.86; O, 13.38; Found: C, 75.46; H, 5.32; N, 5.69; O, 13.26.

Workup

  1. temperaturewas refluxed for 12 hours
  2. filtrationThereafter, the product was filtered
  3. washwashed with water

Sources & evidence

ORD record
ord-b1a1dba925cf4262b0dfd653d22408b6
Source dataset
uspto-grants-1987_02
Patent number
US04645727

Reaction notes

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