反応 #1458416

反応方程式

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

glutaric anhydride

→

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

収率 40.0%

溶媒

tetrahydrofurane

反応条件

後処理

1. 1
   workup.ADDITIONwas added at room temperature
2. 2
   温度The mixture was refluxed for 16 hours
3. 3
   ろ過The mixture was then filtered
4. 4
   その他the solvent was evaporated
5. 5
   workup.DISSOLUTIONthe crude product was dissolved in ethylacetate
6. 6
   抽出extracted three times with a 1N sodium hydroxide solution
7. 7
   その他were acidified with conc. HCI at 0° C
8. 8
   その他A precipitate was formed
9. 9
   ろ過filtration
10. 10
    その他yielded an orange solid
11. 11
    その他The solid so obtained
12. 12
    洗浄was washed with water
13. 13
    その他After drying the product

実験手順

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.

出典