2-Azidomethylanthraquinone → 2-Aminomethylanthraquinone

HRID 231913Notes

Reaction equation

HRID 231913 reaction equation
[N:1]([CH2:4][C:5]1[CH:18]=[CH:17][C:16]2[C:15](=[O:19])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8](=[O:20])[C:7]=2[CH:6]=1)=[N+]=[N-].[H][H]>CN(C=O)C.[Pt]>[NH2:1][CH2:4][C:5]1[CH:18]=[CH:17][C:16]2[C:15](=[O:19])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8](=[O:20])[C:7]=2[CH:6]=1

Participants

5

Reactant 2

HCID 200322122-AzidomethylanthraquinoneHCID 178418361HCID 178418361, compound

Product 1

HCID 199878022-AminomethylanthraquinoneYield 75.9%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6228DimethylformamideSolvent

Procedure

9.5 g of 2-azidomethylanthraquinone are dissolved in 100 ml of DMF, 1.0 g of platinum-on-charcoal catalyst (5% by weight of Pt) is added and hydrogenation is carried out with hydrogen for 15 minutes. The catalyst is filtered off, 200 ml of water are added to the filtrate and the mixture is filtered. The red crystals which have precipitated are recrystallised from dioxane. 6.5 g (70.01% of theory) of 2-aminomethylanthraquinone are obtained; melting point: 170°-78° C.

Workup

  1. filtrationThe catalyst is filtered off
  2. addition200 ml of water are added to the filtrate
  3. filtrationthe mixture is filtered
  4. customThe red crystals which have precipitated
  5. customare recrystallised from dioxane

Sources & evidence

ORD record
ord-f59ab920643c402da667a63e887fafac
Source dataset
uspto-grants-1989_07
Patent number
US04849533

Reaction notes

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