2,6-Dihydroxyanthraquinone → 2,6-Bis(2-morpholinoethoxy)anthraquinone dihydrochloride

HRID 1283220Notes

Reaction equation

HRID 1283220 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.[ClH:19].[Cl:20][CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1.[OH-:29].[K+]>O.C1(C)C=CC=CC=1.ClC1C=CC=CC=1>[ClH:20].[ClH:19].[O:26]1[CH2:27][CH2:28][N:23]([CH2:22][CH2:21][O:1][C:2]2[CH:15]=[CH:14][C:13]3[C:12](=[O:16])[C:11]4[C:6](=[CH:7][CH:8]=[C:9]([O:17][CH2:21][CH2:22][N:23]5[CH2:28][CH2:27][O:29][CH2:25][CH2:24]5)[CH:10]=4)[C:5](=[O:18])[C:4]=3[CH:3]=2)[CH2:24][CH2:25]1

Participants

7

Reactant 3

HCID 67762,6-DihydroxyanthraquinoneHCID 14797Potassium HydroxideHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)

Product 1

HCID 203697702,6-Bis(2-morpholinoethoxy)anthraquinone dihydrochloride

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolvent2×HCID 7964ChlorobenzeneSolvent

Procedure

This compound was prepared by the method of Example 3, with the exception that toluene was used as the reaction medium rather than chlorobenzene, from 36 g. (0.15 mole) of 2,6-dihydroxyanthraquinone, 100 g. (0.54 mole of N-(2-chloroethyl) morpholine hydrochloride, 66g. (1.0 mole) of potassium hydroxide pellets (85%), 400 ml. of toluene and 100 ml. of water. The dihydrochloride salt was recrystallized twice from isopropanol with enough water added to effect solution. The pure compound melted with decomposition at 288°-290°C.; γmax (H2O) 273 mμ, E1cm1% 778.

Workup

  1. customThe dihydrochloride salt was recrystallized twice from isopropanol with enough water
  2. additionadded
  3. custommelted with decomposition at 288°-290°C.

Sources & evidence

ORD record
ord-2f57abf0da3543e4868a1bc045bae37f
Source dataset
uspto-grants-1976_08
Patent number
US03974186

Reaction notes

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