Hydrazine → 2,3,3-Trimethyl-3H-indol-5-amine

HRID 1516869Notes

Reaction equation

HRID 1516869 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([CH3:13])[C:7]2([CH3:15])[CH3:14])([O-])=O.NN>CCO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([CH3:13])[C:7]2([CH3:15])[CH3:14]

Participants

5

Reactant 2

HCID 9321HydrazineHCID 975513H-Indole, 2,3,3-trimethyl-5-nitro-

Product 1

HCID 5945482,3,3-Trimethyl-3H-indol-5-amineYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To the solution of 5-nitro-2,3,3-trimethylindole (1) (10 g) in EtOH (50 mL), hydrazine (35% in water, 6.72 g) was slowly added. The mixture was allowed to stir at room temperature for 10 min followed by the addition of palladium on carbon (Pd/C) (20% Pd/C, 1.30 g). The resultant suspension was heated at 70° C. for 2 hours, filtered, and concentrated to provide the desired product 2 (8.52 g, 100% yield): ESI-MS, Calculated [M+H]+ 175.1, Found 175.1.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-7f423b345c6d4a278dfc5dcff454766c
Source dataset
uspto-grants-2012_07
Patent number
US08227621B2

Reaction notes

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