Ethanol → HCID 67483598, compound

HRID 1166711Notes

Reaction equation

HRID 1166711 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](C(OCC)=O)=[CH:5]2.[NH2:16][NH2:17].[CH2:18]([OH:20])C>>[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[C:18]([NH:16][NH2:17])=[O:20]

Participants

4

Reactant 3

HCID 702EthanolHCID 9321HydrazineHCID 90677Ethyl 5-hydroxy-1H-indole-2-carboxylate

Product 1

HCID 67483598HCID 67483598, compoundYield 85%

Procedure

To a sample of ethyl 5-hydroxyindole-2-carboxylate (5 g, 24 mmol), dissolved in ethanol (250 mL) was added hydrazine (4 mL, 121 mmol). The reaction was refluxed overnight under nitrogen. Upon cooling the reaction vessel, the desired product crystallized. The white solid was isolated by filtration. Recrystallization from hot ethanol gave the 5-hydroxyindole-3-carboxylic acid hydrazide in 85% yield.

Workup

  1. temperatureThe reaction was refluxed overnight under nitrogen
  2. temperatureUpon cooling the reaction vessel
  3. customthe desired product crystallized
  4. customThe white solid was isolated by filtration
  5. customRecrystallization from hot ethanol

Sources & evidence

ORD record
ord-471d6f2d684b40ecad26a488b1e6f365
Source dataset
uspto-grants-2003_09
Patent number
US06613942B1

Reaction notes

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