반응 #534675

반응 방정식

N-benzylisatin

hydrazine hydrate

→

title compound

수율 78.2%

N-Benzyl-oxindole

수율 78.2%

용매

ether pentane

반응 조건

후처리

1. 1
   기타placed in an oil bath
2. 2
   온도After a total of 5 h at 125° C., the mixture was cooled
3. 3
   추출extracted with EtOAc (2×100 mL)
4. 4
   세척The combined organic portions were washed twice with 1.0 M aq. H2SO4
5. 5
   건조once each with half-saturated brine then brine, dried over MgSO4
6. 6
   여과filtered
7. 7
   농축concentrated
8. 8
   기타to afford a pale yellow solid

실험 절차

N-benzylisatin (13.0 g, 55 mmol) was mixed with hydrazine hydrate (60 mL) and placed in an oil bath. The mixture was heated in stages to 125° C., becoming first a green sludge, then yellow with clumps of a sticky solid. After a total of 5 h at 125° C., the mixture was cooled and extracted with EtOAc (2×100 mL). The combined organic portions were washed twice with 1.0 M aq. H2SO4, and once each with half-saturated brine then brine, dried over MgSO4, filtered and concentrated to afford a pale yellow solid. Re-precipitation from ether/pentane gave the title compound as an off-white solid (9.6 g, 75%). Spectral data matches literature values (C. Martin and E. M. Carreira, J. Am. Chem. Soc., 2005, 127, 11505-11515).

출처