Ethanol → HCID 71272686, compound

HRID 475072Notes

Reaction equation

HRID 475072 reaction equation
CO[C:3]1[CH:17]=[CH:16][C:6]([CH2:7][O:8][CH2:9][CH2:10][C:11](=O)[CH2:12][C:13]#[N:14])=[CH:5][CH:4]=1.[OH2:18].[NH2:19][NH2:20].[CH3:21]CO>>[CH3:21][O:18][C:3]1[CH:17]=[CH:16][C:6]([CH2:7][O:8][CH2:9][CH2:10][C:11]2[NH:20][N:19]=[C:13]([NH2:14])[CH:12]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 71272044HCID 71272044, compound

Product 1

HCID 71272686HCID 71272686, compoundYield 80%

Procedure

A mixture of 5-((4-methoxybenzyl)oxy)-3-oxo-pentanenitrile (78 g, 334.4 mmol) and hydrazine hydrate (50 g, 1 mol) in EtOH (500 mL) was heated under reflux for 16 h. After cooling to RT, the solvent was removed in vacuo and the residue was partitioned between DCM (400 mL) and water (400 mL). The organic layer was separated and washed with brine, dried (Na2SO4), and then concentrated in vacuo. The residue was purified by SiO2 chromatography eluting with 5% MeOH/DCM to afford 66 g (80%) of 5-(2-((4-methoxybenzyl)oxy)ethyl)-1H-pyrazol-3-amine as a yellow solid.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 16 h
  3. customthe solvent was removed in vacuo
  4. customthe residue was partitioned between DCM (400 mL) and water (400 mL)
  5. customThe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by SiO2 chromatography
  10. washeluting with 5% MeOH/DCM

Sources & evidence

ORD record
ord-8313f7ce234f45549e7be340ac27772a
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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