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

HRID 556209Notes

Reaction equation

HRID 556209 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=CC=1.[CH:35]([NH2:38])([CH3:37])[CH3:36].[CH2:39]1COCC1>>[CH:35]([NH:38][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]([NH:29][CH:34]([CH3:33])[CH3:39])[CH3:2])[C:12](=[O:28])[C:13]=2[CH:14]=[CH:15][CH:16]=1)=[O:27])([CH3:37])[CH3:36]

Participants

5

Reactant 4

HCID 1049PyridineHCID 6363IsopropylamineHCID 8028TetrahydrofuranHCID 107407551,8-Bis(3-chloropropionamido)anthraquinone2×

Product 1

HCID 669862741,8-Bis[2-(isopropylamino) propionamido]anthraquinoneYield 58%

Procedure

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

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-65b6f80601984b91add077c9f646a4d7
Source dataset
uspto-grants-2011_11
Patent number
US08053583B2

Reaction notes

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