Pyridine → 1,8-Bis[2-(N-ethylmethylamino) propionamido]anthraquinone

HRID 556210Notes

Reaction equation

HRID 556210 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=C[CH:30]=1.[CH2:35]([NH:37][CH3:38])[CH3:36]>C1COCC1>[CH2:34]([N:29]([CH3:30])[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:37]([CH3:38])[CH2:35][CH3:36])[CH3:2])[C:12](=[O:28])[C:13]=2[CH:14]=[CH:15][CH:16]=1)=[O:27])[CH3:33]

Participants

5

Reactant 3

HCID 1049PyridineHCID 12219N-MethylethylamineHCID 107407551,8-Bis(3-chloropropionamido)anthraquinone2×

Product 1

HCID 669867101,8-Bis[2-(N-ethylmethylamino) propionamido]anthraquinoneYield 79%

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 N-ethylmethylamine (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 4k.

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-72a533156583444197ee66c3c3fe84a6
Source dataset
uspto-grants-2011_11
Patent number
US08053583B2

Reaction notes

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