Pyridine → 1,8-Bis[3-(diethylamino) propionamido]anthraquinone

HRID 556206Notes

Reaction equation

HRID 556206 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]=[CH:33]C=[CH:31][CH:30]=1.[CH2:35]([NH:37][CH2:38][CH3:39])[CH3:36]>C1COCC1>[CH2:34]([N:29]([CH2:30][CH3:31])[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][N:37]([CH2:38][CH3:39])[CH2:35][CH3:36])[C:12](=[O:28])[C:11]=2[CH:10]=[CH:9][CH:8]=1)=[O:5])[CH3:33]

Participants

5

Reactant 3

HCID 1049PyridineHCID 8021DiethylamineHCID 107407551,8-Bis(3-chloropropionamido)anthraquinone2×

Product 1

HCID 107674521,8-Bis[3-(diethylamino) propionamido]anthraquinoneYield 72%

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 diethylamine (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 yellow orange compound 4a.

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-24fb0a87635b47cda62fe54c09029da9
Source dataset
uspto-grants-2011_11
Patent number
US08053583B2

Reaction notes

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