Water → 9,10-Anthracenedione, 1,5-bis[(3-hydroxypropyl)amino]-

HRID 389837

Reaction equation

HRID 389837 reaction equation
Cl[C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[C:9](Cl)[CH:10]=[CH:11][CH:12]=3)[C:7](=[O:18])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[NH2:19][CH2:20][CH2:21][CH2:22][OH:23].[OH2:24]>CS(C)=O>[OH:23][CH2:22][CH2:21][CH2:20][NH:19][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[C:9]([NH:19][CH2:20][CH2:21][CH2:22][OH:24])[CH:10]=[CH:11][CH:12]=3)[C:7](=[O:18])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67111,5-DichloroanthraquinoneHCID 90863-Amino-1-propanol

Product 1

HCID 113142159,10-Anthracenedione, 1,5-bis[(3-hydroxypropyl)amino]-

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
130 °C

Procedure

1,5-Dichloroanthraquinone (2.8 g; 10 mmol) is mixed with 3-amino-1-propanol (10 mL) in DMSO (50 mL) and heated to 130° C. for 4 hours. The mixture is cooled to ˜80° and added water (150 mL). When the mixture has reached RT the formed precipitate is isolated by filtration, washed with water (2×50 mL), boiled in toluene (200 mL) and the un-dissolved product is isolated by filtration and dried. Yield: 3.2 g (90%).

Workup

  1. temperatureThe mixture is cooled to ˜80°
  2. customhas reached RT
  3. customis isolated by filtration
  4. washwashed with water (2×50 mL)
  5. customthe un-dissolved product is isolated by filtration
  6. customdried

Sources & evidence

ORD record
ord-f4fc9cd1e26643d986107341a5d6747a
Source dataset
uspto-grants-2013_02
Patent number
US08383344B2

Linked notes

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