反应详情

A 10.0 g sample of 2-chlorophenylhydrazine hydrochloride and 17.9 g of 4-phthalimidobutyraldehyde diethyl acetal were stirred in 200 mL ethanol with 1 mL 5N HCl. The mixture was concentrated to a residue which was slurried in a small amount of methylene chloride. A yellow solid was collected and vacuum dried at 40° C. The solid was stirred in 500 mL ethanol. Hydrazine hydrate (14 g) was added and the mixture was heated at reflux for 14 hours. A 60 mL sample of 5N HCl was added and the mixture was heated at reflux for 1 hour. The mixture was allowed to cool and was concentrated to a residue. The residue was partitioned between 1N NaOH and chloroform. The organic layer was separated and the aqueous layer was extracted with chloroform. The combined extracts were dried (Na2SO4) and concentrated to an oil. The oil was chromatographed on silica gel using a gradient of 0-10% methanol in chloroform containing 0.2% ammonium hydroxide. Fractions containing product were concentrated to an oil which was taken up in a small amount of methanol and added to ethereal HCl. A solid was collected, washed with diethyl ether, and vacuum dried at 50° C.

1. concentrationThe mixture was concentrated to a residue which
2. customA yellow solid was collected
3. customvacuum dried at 40° C
4. additionHydrazine hydrate (14 g) was added
5. temperaturethe mixture was heated
6. temperatureat reflux for 14 hours
7. additionA 60 mL sample of 5N HCl was added
8. temperaturethe mixture was heated
9. temperatureat reflux for 1 hour
10. temperatureto cool
11. concentrationwas concentrated to a residue
12. customThe residue was partitioned between 1N NaOH and chloroform
13. customThe organic layer was separated
14. extractionthe aqueous layer was extracted with chloroform
15. dry with materialThe combined extracts were dried (Na2SO4)
16. concentrationconcentrated to an oil
17. customThe oil was chromatographed on silica gel using a gradient of 0-10% methanol in chloroform containing 0.2% ammonium hydroxide
18. additionFractions containing product
19. concentrationwere concentrated to an oil which
20. additionadded to ethereal HCl
21. customA solid was collected
22. washwashed with diethyl ether, and vacuum
23. customdried at 50° C.