Reaction #1458416

Reaction equation

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

glutaric anhydride

→

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

Yield 40.0%

Solvents

tetrahydrofurane

Conditions

Workup

1. 1
   workup.ADDITIONwas added at room temperature
2. 2
   TemperatureThe mixture was refluxed for 16 hours
3. 3
   FiltrationThe mixture was then filtered
4. 4
   Otherthe 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
   Otherwere acidified with conc. HCI at 0° C
8. 8
   OtherA precipitate was formed
9. 9
   Filtrationfiltration
10. 10
    Otheryielded an orange solid
11. 11
    OtherThe solid so obtained
12. 12
    Washwas washed with water
13. 13
    OtherAfter drying the product

Procedure

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