Réaction #534675

Équation de réaction

N-benzylisatin

hydrazine hydrate

→

title compound

Rendement 78.2%

N-Benzyl-oxindole

Rendement 78.2%

Solvants

ether pentane

Conditions de réaction

Traitement

1. 1
   Autreplaced in an oil bath
2. 2
   TempératureAfter a total of 5 h at 125° C., the mixture was cooled
3. 3
   Extractionextracted with EtOAc (2×100 mL)
4. 4
   LavageThe combined organic portions were washed twice with 1.0 M aq. H2SO4
5. 5
   Séchageonce each with half-saturated brine then brine, dried over MgSO4
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated
8. 8
   Autreto afford a pale yellow solid

Mode opératoire

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).

Source