Reaction #302882

ord-f3325466c0ec494da3cb892c8ffb6c54

Reaction equation

O=C1c2cccc(Cl)c2C(=O)c2cccc(Cl)c21
1,5-Dichloroanthraquinone
NCCCO
3-amino-1-propanol
O
water
O=C1c2cccc(NCCCO)c2C(=O)c2cccc(NCCCO)c21
1,5-Bis(3-hydroxypropylamino)-anthraquinone

Solvents

Conditions

Temperature
130°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    TemperatureThe mixture is cooled to ˜80°
  2. 2
    Otherhas reached RT
  3. 3
    Otheris isolated by filtration
  4. 4
    Washwashed with water (2×50 mL)
  5. 5
    Otherthe un-dissolved product is isolated by filtration
  6. 6
    Otherdried

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%).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08192937B2uspto-grants-2012_06