Hydrazine → 1H-Indole-5-carbohydrazide

HRID 634086Notes

Reaction equation

HRID 634086 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([O:12]C)=O)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[NH2:14][NH2:15]>CCO>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([NH:14][NH2:15])=[O:12])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 2737635methyl 1H-indole-5-carboxylate

Product 1

HCID 227221541H-Indole-5-carbohydrazideYield 77.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of methyl 1H-indole-5-carboxylate (0.9 g, 5.142 mmol) in EtOH (10 mL) was added NH2NH2 (1.8 mL, 38.11 mmol). The reaction was heated at reflux for 12 h. The solvent was removed in vacuo to give a yellow solid, which was recrystallized with 60% EtOAc in n-hexane (10 mL) to afford 1H-indole-5-carbohydrazide (0.7 g, 3.98 mmol, 77.8%). MS (ESI, pos. ion) m/z: 176 (M+1).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 12 h
  3. customThe solvent was removed in vacuo
  4. customto give a yellow solid, which
  5. customwas recrystallized with 60% EtOAc in n-hexane (10 mL)

Sources & evidence

ORD record
ord-d1c652d76c4e4af08c8c7a4bf57bcf47
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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