Ammonia → 9,10-Anthracenedione, 1-amino-5,8-dihydroxy-4-[[2-[(2-hydroxyethyl)amino]ethyl]amino]-, hydrochloride (1:1)

HRID 2296250Notes

Reaction equation

HRID 2296250 reaction equation
O[C:2]1[CH2:3][CH2:4][C:5](O)=[C:6]2[C:15]=1[C:14](=[O:16])[C:13]1[C:8](=[C:9]([OH:18])[CH:10]=[CH:11][C:12]=1[OH:17])[C:7]2=[O:19].[NH2:21][CH2:22][CH2:23][NH:24][CH2:25][CH2:26][OH:27].[NH3:28].C1(Cl)C(=O)C([Cl:37])=C(Cl)C(=O)C=1Cl.Cl>COCCO>[ClH:37].[OH:27][CH2:26][CH2:25][NH:24][CH2:23][CH2:22][NH:21][C:5]1[C:6]2[C:7](=[O:19])[C:8]3[C:13](=[C:12]([OH:17])[CH:11]=[CH:10][C:9]=3[OH:18])[C:14](=[O:16])[C:15]=2[C:2]([NH2:28])=[CH:3][CH:4]=1

Participants

7

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 8112N-(2-Hydroxyethyl)ethylenediamineHCID 8371ChloranilHCID 178515248HCID 178515248, compound

Product 1

HCID 204720689,10-Anthracenedione, 1-amino-5,8-dihydroxy-4-[[2-[(2-hydroxyethyl)amino]ethyl]amino]-, hydrochloride (1:1)

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent3×

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 35 g. (0.10 mole) of 2,3-dihydro-1,4,5,8-tetrahydroxy-9,10-anthracenedione (80% pure) in 750 ml. of methyl cellosolve in an inert, closed atmosphere at 10° C. was slowly added 25 ml. (0.10 mole) of a 4.0 M solution of 2-(2-aminoethylamino)ethanol in methyl cellosolve. The temperature was allowed to rise slowly to 20° C. The solution was then slowly heated to 50° C. and to it was slowly added 75 ml. (0.11 mole) of a 2.2 M solution of ammonia in methyl cellosolve. The mixture was then stirred at 50° C. in this sealed atmosphere for 20 hours. The crude "leuco" intermediate was then filtered as a brown powder. The brown powder was suspended in 500 ml. of methyl cellosolve and oxidized by adding 12 g. (0.10 mole) of chloranil followed by 200 ml. (0.50 mole) of 2.5 N ethanolic hydrogen chloride. The mixture was stirred at 25° C. overnight and was filtered to give 18 g. of blue-black powder. A 7.5 g. portion of this powder was dissolved in 50 ml. of hot water and filtered through a pad of acid-washed Celite. To the hot filtrate was added 50 ml. of ethanol and 50 ml. of tetrahydrofuran. The mixture was cooled and filtered to give 4.4 g. of the desired product as purple-black crystals, mp 276°-280° C.

Workup

  1. customto rise slowly to 20° C
  2. filtrationThe crude "leuco" intermediate was then filtered as a brown powder
  3. additionby adding 12 g
  4. stirringThe mixture was stirred at 25° C. overnight
  5. filtrationwas filtered
  6. customto give 18 g
  7. dissolutionportion of this powder was dissolved in 50 ml
  8. filtrationof hot water and filtered through a pad of acid-washed Celite
  9. additionTo the hot filtrate was added 50 ml
  10. temperatureThe mixture was cooled
  11. filtrationfiltered
  12. customto give 4.4 g

Sources & evidence

ORD record
ord-0af9f40fe94c4166a35ad1ed75741c93
Source dataset
uspto-grants-1984_01
Patent number
US04428882

Reaction notes

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