Ethanol → 5-Methyl-2-furohydrazide

HRID 1889027Notes

Reaction equation

HRID 1889027 reaction equation
[CH3:1][C:2]1OC=[C:4]([C:7]([O:9]C)=O)[CH:3]=1.[OH2:11].[NH2:12][NH2:13].[CH2:14](O)C>>[CH3:14][C:1]1[O:11][C:4]([C:7]([NH:12][NH2:13])=[O:9])=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)2×HCID 23661399Methyl 5-methylfuran-3-carboxylate

Product 1

HCID 41592505-Methyl-2-furohydrazide

Procedure

To a solution of methyl 5-methyl-3-furancarboxylate (0.314 mL, 2.5 mmol, commercially available from e.g. Sigma-Aldrich, Fluorochem or Alfa Aesar) in ethanol (20 mL) was added hydrazine monohydrate (0.093 mL, 3.00 mmol) and the solution was stirred under argon and reflux for 18 hours. Analysis by LCMS and TLC showed starting material to still be present, thus more hydrazine monohydrate (0.275 mL, 8.75 mmol) was added and the solution was further stirred under argon and reflux for 18 hours. The solvent was then evaporated in vacuo to yield the product in 0.341 g.

Workup

  1. temperaturereflux for 18 hours
  2. additionwas added
  3. stirringthe solution was further stirred under argon
  4. temperaturereflux for 18 hours
  5. customThe solvent was then evaporated in vacuo
  6. customto yield the product in 0.341 g

Sources & evidence

ORD record
ord-493fea9f147c41d3a7718f6062e69261
Source dataset
uspto-grants-2013_08
Patent number
US08501946B2

Reaction notes

Loading…