Isopropylamine → 1,8-Bis[2-(Isopropylamino)Acetamido]Anthraquinone

HRID 556203Notes

Reaction equation

HRID 556203 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[C:19]2[C:18](=[O:20])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][C:16]=3[NH:21][C:22](=[O:25])[CH2:23]Cl)[C:11](=[O:26])[C:10]=2[CH:9]=[CH:8][CH:7]=1)=[O:4].[CH:27]([NH2:30])([CH3:29])[CH3:28]>CN(C)C=O>[CH:27]([NH:30][CH2:2][C:3]([NH:5][C:6]1[C:19]2[C:18](=[O:20])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][C:16]=3[NH:21][C:22](=[O:25])[CH2:23][NH:5][CH:6]([CH3:19])[CH3:7])[C:11](=[O:26])[C:10]=2[CH:9]=[CH:8][CH:7]=1)=[O:4])([CH3:29])[CH3:28]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 469280411,8-Bis(chloroacetamido)anthraquinone2×

Product 1

HCID 462448661,8-Bis[2-(Isopropylamino)Acetamido]AnthraquinoneYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Add 0.4 g, 1.0 mmol 1,8-bis(chloroacetamido)anthraquinone (compound 3) with 0.5 ml TEA, and 0.6 ml, 6 mmole isopropylamine, dissolved in 20 ml dehydrated dimethylformamide (DMF). The mixture is reacted in a mini-reactor. The reaction temperature is 120° C. in the oil bath and the reaction time is 30 minutes. The reacted mixture is poured into a little bit ice water and is filtered to collect precipitate. The precipitate is recrystallized from ethanol to get yellow compound 3o.

Workup

  1. customThe mixture is reacted in a mini-reactor
  2. customis 120° C. in the oil bath
  3. filtrationis filtered
  4. customto collect precipitate
  5. customThe precipitate is recrystallized from ethanol

Sources & evidence

ORD record
ord-72974a2bf0424c22873bb7bc2c54f2df
Source dataset
uspto-grants-2011_11
Patent number
US08053583B2

Reaction notes

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