反应详情

温度

125 °C

A solution of tert-butyl N′-[3-(3,3-diethoxypropionylamino)quinolin-4-yl]-hydrazinecarboxylate (13.75 g, 32.9 mmol) and pyridinium p-toluenesulfonate (0.206 g, 0.082 mmol) in 1-propanol (250 mL) was placed under a nitrogen atmosphere and heated to 125° C. After 4 h, the reaction was cooled to ambient temperature and concentrated under reduced pressure to yield a dark red oily solid. This material was suspended in HCl (55 mL, 3 M in ethanol) and heated to 100° C. After 1.5 h, the reaction mix was cooled to ambient temperature and concentrated under reduced pressure to give a brown solid. The solid was suspended in water (50 mL), stirred vigorously, and neutralized with drop-wise addition of 10% NaOH aqueous solution until the pH of the liquid was 8. The aqueous mixture was transferred to a separatory funnel and extracted with chloroform (4×25 mL). The combined organic extracts were concentrated under reduced pressure to give a dark red solid. This solid was purified by prep. HPLC (350 g silica gel eluted with 1-20% CMA in chloroform) to give a dark red solid. This material was triturated with ether (75 mL) and filtered to yield 2.31 g of 10H-pyrazolo[1′,5′:1,2]imidazo[4,5-c]quinoline as a red solid.

1. temperaturethe reaction was cooled to ambient temperature
2. concentrationconcentrated under reduced pressure
3. customto yield a dark red oily solid
4. temperatureheated to 100° C
5. waitAfter 1.5 h
6. additionthe reaction mix
7. temperaturewas cooled to ambient temperature
8. concentrationconcentrated under reduced pressure
9. customto give a brown solid
10. customThe aqueous mixture was transferred to a separatory funnel
11. extractionextracted with chloroform (4×25 mL)
12. concentrationThe combined organic extracts were concentrated under reduced pressure
13. customto give a dark red solid
14. customThis solid was purified by prep
15. washHPLC (350 g silica gel eluted with 1-20% CMA in chloroform)
16. customto give a dark red solid
17. customThis material was triturated with ether (75 mL)
18. filtrationfiltered