Реакция #1458416

Уравнение реакции

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

glutaric anhydride

→

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

Выход 40.0%

Растворители

tetrahydrofurane

Условия реакции

Обработка

1. 1
   workup.ADDITIONwas added at room temperature
2. 2
   ТемператураThe mixture was refluxed for 16 hours
3. 3
   ФильтрацияThe mixture was then filtered
4. 4
   Другоеthe solvent was evaporated
5. 5
   workup.DISSOLUTIONthe crude product was dissolved in ethylacetate
6. 6
   Экстракцияextracted three times with a 1N sodium hydroxide solution
7. 7
   Другоеwere acidified with conc. HCI at 0° C
8. 8
   ДругоеA precipitate was formed
9. 9
   Фильтрацияfiltration
10. 10
    Другоеyielded an orange solid
11. 11
    ДругоеThe solid so obtained
12. 12
    Промывкаwas washed with water
13. 13
    ДругоеAfter drying the product

Методика

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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