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

HRID 616342

Reaction equation

HRID 616342 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 dihydrocholoride salt was recrystallized twice from isopropanol with enough water added to effect solution. The pure compound melted with decomposition at 288-290° C.; λmax (H2 0) 273 μ, E1cm.1% 778.

Workup

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

Sources & evidence

ORD record
ord-82cee194515f4adb839daa1a4052b408
Source dataset
uspto-grants-1978_02
Patent number
US04073904

Linked notes

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