2,6-Dihydroxyanthraquinone → 2,6-Bis[2-(diethylamino)ethoxy]anthracene-9,10-dione--hydrogen chloride (1/2)

HRID 1283217Notes

Reaction equation

HRID 1283217 reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][C:13]2[C:12](=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([OH:17])[CH:10]=3)[C:5](=[O:18])[C:4]=2[CH:3]=1.[C:19]1([CH3:26])C(C)=CC=CC=1.[ClH:27].[CH2:28]([N:30]([CH2:34][CH3:35])[CH2:31][CH2:32][Cl:33])[CH3:29]>O>[ClH:33].[ClH:27].[CH2:28]([N:30]([CH2:19][CH3:26])[CH2:31][CH2:32][O:1][C:2]1[CH:15]=[CH:14][C:13]2[C:12](=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([O:17][CH2:29][CH2:28][N:30]([CH2:34][CH3:35])[CH2:31][CH3:32])[CH:10]=3)[C:5](=[O:18])[C:4]=2[CH:3]=1)[CH3:29]

Participants

5

Reactant 3

HCID 67762,6-DihydroxyanthraquinoneHCID 7237O-XyleneHCID 133631-Chloro-2-(diethylamine)ethane hydrochloride

Product 1

HCID 681397362,6-Bis[2-(diethylamino)ethoxy]anthracene-9,10-dione--hydrogen chloride (1/2)

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred suspension of 30 g. of the powdered diphenoxide, containing about 24 g. (0.075 mole) of the dipotassium salt of 2,6-dihydroxyanthraquinone, in 200 ml. of xylene was heated to reflux and a small amount of water collected in the Dean-Stark distilling receiver. A solution of 2-diethylaminoethyl chloride in 100 ml. of xylene, prepared as in Example 1 from 50 g. (0.29 mole) of 2-diethylaminoethyl chloride hydrochloride, was then added and the resulting mixture heated to reflux for about 24 hours. The reaction mixture was poured into water and worked up exactly as in Example 1.

Workup

  1. additionA stirred suspension of 30 g
  2. temperatureto reflux
  3. customa small amount of water collected in the Dean-Stark
  4. distillationdistilling receiver
  5. customof xylene, prepared as in Example 1 from 50 g
  6. temperaturethe resulting mixture heated
  7. temperatureto reflux for about 24 hours

Sources & evidence

ORD record
ord-b9433c3610aa4b598df595b3f40ae8f1
Source dataset
uspto-grants-1976_08
Patent number
US03974186

Reaction notes

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