Reacción #1458416

Ecuación de reacción

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

glutaric anhydride

→

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

Rendimiento 40.0%

Disolventes

tetrahydrofurane

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added at room temperature
2. 2
   TemperaturaThe mixture was refluxed for 16 hours
3. 3
   FiltraciónThe mixture was then filtered
4. 4
   Otrothe solvent was evaporated
5. 5
   workup.DISSOLUTIONthe crude product was dissolved in ethylacetate
6. 6
   Extracciónextracted three times with a 1N sodium hydroxide solution
7. 7
   Otrowere acidified with conc. HCI at 0° C
8. 8
   OtroA precipitate was formed
9. 9
   Filtraciónfiltration
10. 10
    Otroyielded an orange solid
11. 11
    OtroThe solid so obtained
12. 12
    Lavadowas washed with water
13. 13
    OtroAfter drying the product

Procedimiento

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.

Fuente