1,8-Diamino-9,10-anthracenedione → 1,8-Bis(3-chloropropionamido)anthraquinone

HRID 556205

Reaction equation

HRID 556205 reaction equation
[NH2:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][C:12]=3[NH2:17])[C:7](=[O:18])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[Cl:19][CH2:20][CH2:21][C:22](Cl)=[O:23]>CN(C)C=O.N1C=CC=CC=1>[Cl:19][CH2:20][CH2:21][C:22]([NH:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][C:12]=3[NH:17][C:22](=[O:23])[CH2:21][CH2:20][Cl:19])[C:7](=[O:18])[C:6]=2[CH:5]=[CH:4][CH:3]=1)=[O:23]

Participants

5

Reactant 2

HCID 85111,8-Diamino-9,10-anthracenedioneHCID 693643-Chloropropionyl chloride

Product 1

HCID 107407551,8-Bis(3-chloropropionamido)anthraquinoneYield 58%

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

Dissolve 1,8-diaminoanthraquinone (0.476 g, 2 mmol) in N,N-dimethylformamide (20 ml). Add pyridine (0.5 ml) as catalyst in an ice bath and then add 3-chloropropioyl chloride (0.6 ml, 6 mmol). Remove the ice bath, introduce nitrogen, protect from light, and stir the solution at room temperature for one day. The reacted mixture is poured into ice water and filtered to get precipitate. The precipitate is recrystallized from ethanol to obtain orange compound 4.

Workup

  1. customRemove the ice bath
  2. additionintroduce nitrogen
  3. additionThe reacted mixture is poured into ice water
  4. filtrationfiltered
  5. customto get precipitate
  6. customThe precipitate is recrystallized from ethanol

Sources & evidence

ORD record
ord-7128a3e17df04099b9867a2f2d98eb81
Source dataset
uspto-grants-2011_11
Patent number
US08053583B2

Linked notes

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