Hydrazine hydrate (1:1) → 1H-Indole-5-carbohydrazide

HRID 2388583Notes

Reaction equation

HRID 2388583 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.O.[NH2:15][NH2:16]>C(O)C>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([NH:15][NH2:16])=[O:12])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 2737635methyl 1H-indole-5-carboxylate

Product 1

HCID 227221541H-Indole-5-carbohydrazide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 100 mL round bottomed flask was charged with methyl 1H-indole-5-carboxylate (1.6 g, 9.13 mmol) and ethanol (20 mL). To this was added hydrazine monohydrate (10 g) and the mixture was placed under reflux for 7 days. The reaction mixture was concentrated to dryness and chloroform (80 mL) was added. The mixture was decanted and the insoluble white residue was washed once more with chloroform to remove traces of starting material. The white solid (1.54 g, 96%) was dried en vacuo and 1H NMR analysis was consistent with the title compound. 1H NMR (DMSO d6, 400 MHz) δ 10.7 (br s, 1H), 9.6 (br s, 2H), 8.21-8.15 (m, 1H), 7.71 (dd, J=8.6 and 1.7 Hz, 1H), 7.50 (d, J=8.6 Hz, 1H), 7.44-7.39 (m, 1H) and 6.58-6.53 (m, 1H).

Workup

  1. temperatureunder reflux for 7 days
  2. concentrationThe reaction mixture was concentrated to dryness and chloroform (80 mL)
  3. additionwas added
  4. customThe mixture was decanted
  5. washthe insoluble white residue was washed once more with chloroform
  6. customto remove traces of starting material
  7. dry with materialThe white solid (1.54 g, 96%) was dried en vacuo and 1H NMR analysis

Sources & evidence

ORD record
ord-a32ec36fb91d4d7585b6098491462bb9
Source dataset
uspto-grants-2012_09
Patent number
US08268872B2

Reaction notes

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