Ethylamine → 1-[(3-Dimethylaminopropyl)amino]-4-ethylamino-5,8-dihydroxyanthraquinone

HRID 2296249Notes

Reaction equation

HRID 2296249 reaction equation
[CH2:1]1[C:15](=O)[C:14]2[C:5](=[C:6]([OH:20])[C:7]3[C:12]([C:13]=2[OH:17])=[C:11]([OH:18])[CH:10]=[CH:9][C:8]=3[OH:19])[C:3](=O)[CH2:2]1.[CH2:21]([NH2:23])[CH3:22].S(S([O-])=O)([O-])=O.[Na+].[Na+].[CH3:32][N:33]([CH2:35][CH2:36][CH2:37][NH2:38])[CH3:34]>CO>[CH3:32][N:33]([CH3:34])[CH2:35][CH2:36][CH2:37][NH:38][C:15]1[C:14]2[C:13](=[O:17])[C:12]3[C:7](=[C:8]([OH:19])[CH:9]=[CH:10][C:11]=3[OH:18])[C:6](=[O:20])[C:5]=2[C:3]([NH:23][CH2:21][CH3:22])=[CH:2][CH:1]=1

Participants

6

Reactant 4

HCID 6341EthylamineHCID 7993N,N-Dimethyl-1,3-propanediamineHCID 24489Sodium DithioniteHCID 664859,10-Anthracenedione, 2,3-dihydro-1,4,5,8-tetrahydroxy-

Product 1

HCID 204720661-[(3-Dimethylaminopropyl)amino]-4-ethylamino-5,8-dihydroxyanthraquinone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2.74 g. of leuco-1,4,5,8-tetrahydroxyanthraquinone, 0.45 g. of ethylamine, a trace of sodium hydrosulfite and 60 ml. of aqueous methanol was stirred and warmed to 50° C. for one hour. To this was added 1.1 g. of dimethylaminopropylamine and the mixture was stirred and warmed at 50°-60° C. for 2 hours. Air was bubbled through this mixture while heating on a steambath for 6 hours. The mixture was cooled and the title product was collected.

Workup

  1. additionA mixture of 2.74 g
  2. additionTo this was added 1.1 g
  3. temperaturewarmed at 50°-60° C. for 2 hours
  4. customAir was bubbled through this mixture
  5. temperaturewhile heating on a steambath for 6 hours
  6. temperatureThe mixture was cooled
  7. customthe title product was collected

Sources & evidence

ORD record
ord-7a207cab7520465ea39dc06fd5666876
Source dataset
uspto-grants-1984_01
Patent number
US04428882

Reaction notes

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