2-Hydrazinoethanol → 2-(5-Amino-3-methyl-1H-pyrazol-1-yl)ethan-1-ol

HRID 479262Notes

Reaction equation

HRID 479262 reaction equation
[NH2:1]/[C:2](/[CH3:6])=[CH:3]\[C:4]#[N:5].[OH:7][CH2:8][CH2:9][NH:10]N>C(O)CCCC>[NH2:5][C:4]1[N:10]([CH2:9][CH2:8][OH:7])[N:1]=[C:2]([CH3:6])[CH:3]=1

Participants

4

Reactant 2

HCID 80172-HydrazinoethanolHCID 5325263(2Z)-3-Amino-2-butenenitrile

Product 1

HCID 50183732-(5-Amino-3-methyl-1H-pyrazol-1-yl)ethan-1-olYield 63.8%

Reagents, catalysts & solvents 1

HCID 62761-PentanolSolvent

Procedure

To a solution of 16.4 g (0.2 mol) of 3-aminocrotononitrile in 100 cm3 of n-pentanol were added 16.7 g (0.22 mol) of β-hydroxyethylhydrazine and the mixture was then heated at reflux for 12 hours. The n-pentanol was subsequently distilled off under reduced pressure. A thick oil was obtained, which crystallizes by addition of 150 cm3 of isopropyl ether. A beige solid was obtained, which was filtered off on a sinter funnel. After drying under vacuum at 40° C., 18 g of the expected product were obtained in the form of a beige solid, the melting point of which was from 66 to 68° C.

Workup

  1. temperaturethe mixture was then heated
  2. temperatureat reflux for 12 hours
  3. distillationThe n-pentanol was subsequently distilled off under reduced pressure
  4. customA thick oil was obtained
  5. customwhich crystallizes by addition of 150 cm3 of isopropyl ether
  6. customA beige solid was obtained
  7. filtrationwhich was filtered off on a sinter funnel
  8. customAfter drying under vacuum at 40° C.

Sources & evidence

ORD record
ord-104b9bcb8ec74cfebadf190a17fb82e6
Source dataset
uspto-grants-2003_11
Patent number
US06645258B2

Reaction notes

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