Reaction #334220

Reaction equation

2-hydroxyethylhydrazine

ethoxymethylenemalononitrile

→

5-amino-4-cyano-1-(2-hydroxyethyl)pyrazole

Yield 70.3%

Solvents

EtOH

EtOH

Conditions

Workup

1. 1
   workup.ADDITIONwas added over a period of ten minutes
2. 2
   WashThe last of this material was washed into the reaction flask with EtOH (50 ml.)
3. 3
   Temperaturethe mixture was heated
4. 4
   Temperatureunder reflux for 2.5 hours
5. 5
   OtherThe golden-brown crystals which formed
6. 6
   Filtrationwere collected by filtration
7. 7
   Washwashed with ether
8. 8
   Otherdried in vacuo at room temperature

Procedure

A solution of 2-hydroxyethylhydrazine (38.9 g.) in EtOH (425 ml.) was heated to 50° while a solution of ethoxymethylenemalononitrile (52 g.) in warm EtOH (250 ml.) was added over a period of ten minutes. The last of this material was washed into the reaction flask with EtOH (50 ml.), and the mixture was heated under reflux for 2.5 hours. The resulting solution was allowed to cool to room temperature overnight. The golden-brown crystals which formed were collected by filtration, washed with ether, and dried in vacuo at room temperature to give 5-amino-4-cyano-1-(2-hydroxyethyl)pyrazole (45.57 g.): m.p. 158°-160 °.

Source