Hydrazine → 5-Aminoindole

HRID 1798023Notes

Reaction equation

HRID 1798023 reaction equation
NN.[N+:3]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]=[CH:9]2)([O-])=O>[Pd].C(O)C>[NH2:3][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]=[CH:9]2

Participants

5

Reactant 2

HCID 9321HydrazineHCID 225235-Nitroindole

Product 1

HCID 788675-AminoindoleYield 81%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

25 mL of hydrazine (98-100%) are added slowly to a mixture of 25.0 g of 5-nitroindole, 1.2 g of 10% palladium on carbon and 200 mL of absolute ethanol. After the addition, the resulting reaction mixture is then taken to reflux for 2 hours. The catalyst is eliminated by filtration and the filtrate is evaporated in order to produce a solid yellow residue. The crystals are washed with 200 ml of water and they are dried under vacuum in order to produce 16.5 g (81%) of 5-aminoindole. Melting point: 131-134° C.

Workup

  1. additionAfter the addition
  2. customthe resulting reaction mixture
  3. temperatureto reflux for 2 hours
  4. filtrationThe catalyst is eliminated by filtration
  5. customthe filtrate is evaporated in order
  6. customto produce a solid yellow residue
  7. washThe crystals are washed with 200 ml of water and they
  8. customare dried under vacuum in order

Sources & evidence

ORD record
ord-4fc225f16e504acbb4bdf4b22be89c3a
Source dataset
uspto-grants-2013_01
Patent number
US08343964B2

Reaction notes

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