Dipropylamine → 1,8-Bis[2-(Dipropylamino)Acetamido]Anthraquinone

HRID 556202Notes

Reaction equation

HRID 556202 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[C:19]2[C:18](=[O:20])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][C:16]=3[NH:21][C:22](=[O:25])[CH2:23]Cl)[C:11](=[O:26])[C:10]=2[CH:9]=[CH:8][CH:7]=1)=[O:4].[CH2:27]([NH:30][CH2:31][CH2:32][CH3:33])[CH2:28][CH3:29]>CN(C)C=O>[CH2:27]([N:30]([CH2:31][CH2:32][CH3:33])[CH2:2][C:3]([NH:5][C:6]1[C:19]2[C:18](=[O:20])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][C:16]=3[NH:21][C:22](=[O:25])[CH2:23][N:30]([CH2:31][CH2:32][CH3:33])[CH2:27][CH2:28][CH3:29])[C:11](=[O:26])[C:10]=2[CH:9]=[CH:8][CH:7]=1)=[O:4])[CH2:28][CH3:29]

Participants

4

Reactant 2

HCID 8902DipropylamineHCID 469280411,8-Bis(chloroacetamido)anthraquinone2×

Product 1

HCID 462447771,8-Bis[2-(Dipropylamino)Acetamido]AnthraquinoneYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Add 0.4 g, 1.0 mmol 1,8-bis(chloroacetamido)anthraquinone (compound 3) with 0.5 ml TEA, and 0.7 ml, 6 mmole Dipropylamine, dissolved in 20 ml dehydrated dimethylformamide (DMF). The mixture is reacted in a mini-reactor. The reaction temperature is 120° C. in the oil bath and the reaction time is 30 minutes. The reacted mixture is poured into 50 ml ice water and is filtered to collect precipitate. The precipitate is recrystallized from ethanol to get yellow compound 3n.

Workup

  1. customThe mixture is reacted in a mini-reactor
  2. customis 120° C. in the oil bath
  3. filtrationis filtered
  4. customto collect precipitate
  5. customThe precipitate is recrystallized from ethanol

Sources & evidence

ORD record
ord-b0fce5ff57384eaaacfe7ea234a68a37
Source dataset
uspto-grants-2011_11
Patent number
US08053583B2

Reaction notes

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