Reaction #41196

Reaction equation

cyclobutanone

hydrazinecarboxylic acid tert-butyl ester

→

N′-cyclobutylidene-hydrazinecarboxylic acid tert-butyl ester

Yield 81.2%

Solvents

hexane

Conditions

Workup

1. 1
   Temperaturewas heated
2. 2
   Temperatureto reflux for 2 hours
3. 3
   TemperatureAfter cooling down
4. 4
   Othera precipitate formed
5. 5
   Filtrationthe solid was filtered under vacuum
6. 6
   workup.ADDITIONIsopropanol (10 mL) and hexane (100 mL) were added to the solid
7. 7
   Otherthe mixture was put on the rotary evaporator under vacuum until a slurry
8. 8
   FiltrationAfter filtration
9. 9
   Washthe solid was washed with hexane twice
10. 10
    Otherdried in vacuo

Procedure

The reaction mixture of cyclobutanone (15 g, 214 mmol) and hydrazinecarboxylic acid tert-butyl ester (28.3 g, 214 mmol) in hexane (225 mL) was heated to reflux for 2 hours. After cooling down, a precipitate formed and the solid was filtered under vacuum. Isopropanol (10 mL) and hexane (100 mL) were added to the solid and the mixture was put on the rotary evaporator under vacuum until a slurry was generated. After filtration, the solid was washed with hexane twice and dried in vacuo to afford N′-cyclobutylidene-hydrazinecarboxylic acid tert-butyl ester (32 g, 81%) as white solid which was used without further purification.

Source