Reaktion #1458416

Reaktionsgleichung

2,6-diamino-3-((pyridin-3-yl)azo)pyridine

glutaric anhydride

→

5-[(6-amino-5-(3-pyridinyldiazenyl)-2-pyridinyl)amino]-5-oxopentanoic acid

Ausbeute 40.0%

Lösungsmittel

tetrahydrofurane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added at room temperature
2. 2
   TemperaturThe mixture was refluxed for 16 hours
3. 3
   FiltrationThe mixture was then filtered
4. 4
   Sonstigethe solvent was evaporated
5. 5
   workup.DISSOLUTIONthe crude product was dissolved in ethylacetate
6. 6
   Extraktionextracted three times with a 1N sodium hydroxide solution
7. 7
   Sonstigewere acidified with conc. HCI at 0° C
8. 8
   SonstigeA precipitate was formed
9. 9
   Filtrationfiltration
10. 10
    Sonstigeyielded an orange solid
11. 11
    SonstigeThe solid so obtained
12. 12
    Waschenwas washed with water
13. 13
    SonstigeAfter drying the product

Vorschrift

To a mixture of 3.21 g (15 mmol) of 2,6-diamino-3-((pyridin-3-yl)azo)pyridine and 0.27 g (2.2 mmol) of N,N-dimethylamino-pyridine in 100 ml of tetrahydrofurane, 4.27 g (37.5 mmol) of glutaric anhydride was added at room temperature. The mixture was refluxed for 16 hours. The mixture was then filtered, the solvent was evaporated and the crude product was dissolved in ethylacetate and extracted three times with a 1N sodium hydroxide solution. The combined aqueous extracts were acidified with conc. HCI at 0° C. A precipitate was formed, and filtration yielded an orange solid. The solid so obtained was washed with water. After drying the product was recristallised in methanol/water mixture and 1.9 g (40% yield) of 5-[(6-amino-5-(3-pyridinyldiazenyl)-2-pyridinyl)amino]-5-oxopentanoic acid were obtained.

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