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

HRID 464105Notes

Reaction equation

HRID 464105 reaction equation
C(O[CH:4]=[C:5]([C:8]#[N:9])[C:6]#[N:7])C.[OH:10][CH2:11][CH2:12][NH:13][NH2:14]>C(O)C>[NH2:9][C:8]1[N:13]([CH2:12][CH2:11][OH:10])[N:14]=[CH:4][C:5]=1[C:6]#[N:7]

Participants

4

Reactant 2

HCID 80172-HydrazinoethanolHCID 671522-(Ethoxymethylene)propanedinitrile

Product 1

HCID 2198525-amino-1-(2-hydroxyethyl)-1H-pyrazole-4-carbonitrileYield 82.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A procedure analogous to that described in Example 1 was followed except 20.0 g (164 mM) of ethoxymethylene malononitrile in 250 ml of warm ethanol were added to 13.4 ml (15.0 g, 197 mM) of 2-hydroxyethylhydrazine in 30 ml of ethanol maintained at 45°-50°. Following completion of the reaction and subsequent cooling of the mixture, the crystalline product was removed by filtration, and washed with ether to afford 20.5 g (82%) of the title compound: mp, 160°-161°: tlc, Rf =0.28, silica gel, ethyl acetate (100%).

Workup

  1. temperaturemaintained at 45°-50°
  2. customcompletion of the reaction
  3. temperaturesubsequent cooling of the mixture
  4. customthe crystalline product was removed by filtration
  5. washwashed with ether

Sources & evidence

ORD record
ord-6f8781c3366d43df940ae03eed571603
Source dataset
uspto-grants-1985_10
Patent number
US04546104

Reaction notes

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