Pyridine → 1,8-Bis[2-(Isobutylamino)Acetamido]Anthraquinone

HRID 556199Notes

Reaction equation

HRID 556199 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].[N:27]1[CH:32]=[CH:31][CH:30]=CC=1.[CH2:33]([NH2:37])[CH:34]([CH3:36])[CH3:35].[CH3:38]N(C)C=O>>[CH2:33]([NH:37][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:27][CH2:32][CH:31]([CH3:30])[CH3:38])[C:11](=[O:26])[C:10]=2[CH:9]=[CH:8][CH:7]=1)=[O:4])[CH:34]([CH3:36])[CH3:35]

Participants

5

Reactant 4

HCID 1049PyridineHCID 6228DimethylformamideHCID 6558IsobutylamineHCID 469280411,8-Bis(chloroacetamido)anthraquinone2×

Product 1

HCID 462447741,8-Bis[2-(Isobutylamino)Acetamido]AnthraquinoneYield 40%

Procedure

Add 0.4 g, 1.0 mmol 1,8-bis(chloroacetamido)anthraquinone (compound 3) with pyridine (0.5 ml), and 0.6 ml, 6 mmole Isobutylamine, 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 50 ml ice water and is filtered to collect precipitate. The precipitate is recrystallized from ethanol to get yellow compound 3k.

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-00e4a8deecdb438ead2a29856169bd86
Source dataset
uspto-grants-2011_11
Patent number
US08053583B2

Reaction notes

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