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

HRID 556208Notes

Reaction equation

HRID 556208 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][CH:32]=[CH:31][CH:30]=1.[CH2:35]([NH:38][CH2:39][CH2:40][CH3:41])[CH2:36][CH3:37].[CH2:42]1COCC1>>[CH2:34]([N:29]([CH2:30][CH2:31][CH3:42])[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:38]([CH2:39][CH2:40][CH3:41])[CH2:35][CH2:36][CH3:37])[CH3:2])[C:12](=[O:28])[C:13]=2[CH:14]=[CH:15][CH:16]=1)=[O:27])[CH2:33][CH3:32]

Participants

5

Reactant 4

HCID 1049PyridineHCID 8028TetrahydrofuranHCID 8902DipropylamineHCID 107407551,8-Bis(3-chloropropionamido)anthraquinone2×

Product 1

HCID 669863021,8-Bis[2-(dipropylamino) propionamido]anthraquinoneYield 79%

Procedure

Add 1,8-Bis(3-chloropropionamido)anthraquinone (compound 4, 0.42 g, 1.0 mmol) with pyridine (0.5 ml) and dipropylamine (0.7 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 4g.

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-e6149414ab4b4e168025f080d209000a
Source dataset
uspto-grants-2011_11
Patent number
US08053583B2

Reaction notes

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