Réaction #1458416

Équation de réaction

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

glutaric anhydride

→

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

Rendement 40.0%

Solvants

tetrahydrofurane

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwas added at room temperature
2. 2
   TempératureThe mixture was refluxed for 16 hours
3. 3
   FiltrationThe mixture was then filtered
4. 4
   Autrethe solvent was evaporated
5. 5
   workup.DISSOLUTIONthe crude product was dissolved in ethylacetate
6. 6
   Extractionextracted three times with a 1N sodium hydroxide solution
7. 7
   Autrewere acidified with conc. HCI at 0° C
8. 8
   AutreA precipitate was formed
9. 9
   Filtrationfiltration
10. 10
    Autreyielded an orange solid
11. 11
    AutreThe solid so obtained
12. 12
    Lavagewas washed with water
13. 13
    AutreAfter drying the product

Mode opératoire

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.

Source