2-Hydrazinoethanol → 5-amino-1-(2-hydroxyethyl)-1H-pyrazole-4-carbonitrile

HRID 247038Notes

Reaction equation

HRID 247038 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][NH2:5].C(O[CH:9]=[C:10]([C:13]#[N:14])[C:11]#[N:12])C>CCO>[NH2:14][C:13]1[N:4]([CH2:3][CH2:2][OH:1])[N:5]=[CH:9][C:10]=1[C:11]#[N:12]

Participants

4

Reactant 2

HCID 80172-HydrazinoethanolHCID 671522-(Ethoxymethylene)propanedinitrile

Product 1

HCID 2198525-amino-1-(2-hydroxyethyl)-1H-pyrazole-4-carbonitrileYield 70.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

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 °.

Workup

  1. additionwas added over a period of ten minutes
  2. washThe last of this material was washed into the reaction flask with EtOH (50 ml.)
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 2.5 hours
  5. customThe golden-brown crystals which formed
  6. filtrationwere collected by filtration
  7. washwashed with ether
  8. customdried in vacuo at room temperature

Sources & evidence

ORD record
ord-dd52da460f2e4093a26197fdef76c87d
Source dataset
uspto-grants-1987_11
Patent number
US04705793

Reaction notes

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