Dimethylamine → 1,8-Bis[2-(dimethylamino) propionamido]anthraquinone

HRID 556207Notes

Reaction equation

HRID 556207 reaction equation
Cl[CH2:2][CH2:3][C:4]([NH:6][C:7]1[C:20]2[C:19](=[O:21])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][C:17]=3[NH:22][C:23](=[O:27])[CH2:24][CH2:25]Cl)[C:12](=[O:28])[C:11]=2[CH:10]=[CH:9][CH:8]=1)=[O:5].[N:29]1[CH:34]=CC=C[CH:30]=1.[CH3:35][NH:36][CH3:37]>C1COCC1>[CH3:30][N:29]([CH3:34])[CH:24]([CH3:25])[C:23]([NH:22][C:17]1[C:18]2[C:19](=[O:21])[C:20]3[C:11](=[CH:10][CH:9]=[CH:8][C:7]=3[NH:6][C:4](=[O:5])[CH:3]([N:36]([CH3:37])[CH3:35])[CH3:2])[C:12](=[O:28])[C:13]=2[CH:14]=[CH:15][CH:16]=1)=[O:27]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 1049PyridineHCID 107407551,8-Bis(3-chloropropionamido)anthraquinone2×

Product 1

HCID 669864571,8-Bis[2-(dimethylamino) propionamido]anthraquinoneYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add 1,8-Bis(3-chloropropionamido)anthraquinone (compound 4, 0.42 g, 1.0 mmol) with pyridine (0.5 ml) and dimethylamine (0.6 ml, 6 mmole), dissolved in 20 ml dehydrated THF. The mixture is reacted in a mini-reactor. The reaction temperature is 70-80° C. in an oil bath and the reaction time is 6 hours. The reacted mixture is poured into 50 ml ice water, extracted with ethyl acetate and recrystallized from ethanol to get compound 4f.

Workup

  1. dissolutiondissolved in 20 ml
  2. customThe mixture is reacted in a mini-reactor
  3. customThe reaction temperature is 70-80° C. in an oil bath
  4. extractionextracted with ethyl acetate
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-663dd4199d654eb6a0db3b48182d9255
Source dataset
uspto-grants-2011_11
Patent number
US08053583B2

Reaction notes

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