2,6-Dihydroxyanthraquinone → 2,6-Bis(2-(dimethylamino)ethoxy)anthraquinone dihydrochloride

HRID 1283219Notes

Reaction equation

HRID 1283219 reaction equation
O[C:2]1[CH:15]=[CH:14][C:13]2[C:12](=O)[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.[CH3:19][O-:20].[Na+].[ClH:22].[CH3:23][N:24]([CH3:28])[CH2:25][CH2:26][Cl:27].[OH-:29].[Na+]>O.CO.ClC1C=CC=CC=1>[ClH:27].[ClH:22].[CH3:23][N:24]([CH3:28])[CH2:25][CH2:19][O:20][C:2]1[CH:3]=[CH:4][C:13]2[C:12](=[O:29])[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([O:17][CH2:26][CH2:25][N:24]([CH3:28])[CH3:23])[CH:10]=3)[C:5](=[O:18])[C:14]=2[CH:15]=1

Participants

8

Reactant 4

HCID 67762,6-DihydroxyanthraquinoneHCID 14798Sodium HydroxideHCID 10942334Sodium MethoxideHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

HCID 162050882,6-Bis(2-(dimethylamino)ethoxy)anthraquinone dihydrochloride

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 7964ChlorobenzeneSolvent

Procedure

A well-stirred mixture of 12 g. (0.05 mole) of 2,6-dihydroxyanthraquinone, 400 ml. of chlorobenzene, 50 ml of methanol, and 5.4 g. (0.10 mole) of sodium methoxide was heated to boiling, and the methanol distilled from the mixture. When the boiling point of the distillate had reached about 130°C., the mixture was allowed to cool below 100°. Then, a solution of 2-dimethylaminoethyl chloride in 200 ml. of chlorobenzene, prepared from 43.2 g. (0.30 mole) of 2-dimethylaminoethyl chloride hydrochloride, was added and the resulting mixture heated to reflux with continued stirring for 24 hours. When cool, the mixture was poured into 400 ml. of about one per cent sodium hydroxide solution. The aqueous layer was extracted with chloroform. The combined organic fractions were washed well with water, dried over anhydrous magnesium sulfate, filtered, and the solvents removed under reduced pressure in a rotary evaporator. The residue was dissolved in isopropanol and the solution acidified to Congo Red by the addition of ethereal hydrogen chloride. The dihydrochloride salt was recrystallized again from isopropanol to give the pure compound, M.P. 278°-280°C. (dec.) γmax. (H2O) 273 mμ, E1cm1% 967.

Workup

  1. additionA well-stirred mixture of 12 g
  2. distillationthe methanol distilled from the mixture
  3. customhad reached about 130°C.
  4. temperatureto cool below 100°
  5. customof chlorobenzene, prepared from 43.2 g
  6. temperaturethe resulting mixture heated
  7. temperatureto reflux
  8. temperatureWhen cool
  9. additionthe mixture was poured into 400 ml
  10. extractionThe aqueous layer was extracted with chloroform
  11. washThe combined organic fractions were washed well with water
  12. dry with materialdried over anhydrous magnesium sulfate
  13. filtrationfiltered
  14. customthe solvents removed under reduced pressure in a rotary evaporator
  15. dissolutionThe residue was dissolved in isopropanol
  16. additionthe solution acidified to Congo Red by the addition of ethereal hydrogen chloride
  17. customThe dihydrochloride salt was recrystallized again from isopropanol
  18. customto give the pure compound, M.P. 278°-280°C. (dec.) γmax

Sources & evidence

ORD record
ord-3a74a4007a3a44ca947075cd3ff99044
Source dataset
uspto-grants-1976_08
Patent number
US03974186

Reaction notes

Loading…