Hydrazine → 5-amino-1H-indole-7-carbonitrile

HRID 2086042Notes

Reaction equation

HRID 2086042 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([N+:12]([O-])=O)[CH:6]=[C:7]2[C:11]=1[NH:10][CH:9]=[CH:8]2)#[N:2].NN>CO.[Pd]>[C:1]([C:3]1[CH:4]=[C:5]([NH2:12])[CH:6]=[C:7]2[C:11]=1[NH:10][CH:9]=[CH:8]2)#[N:2]

Participants

5

Reactant 2

HCID 9321HydrazineHCID 154534677-Cyano-5-nitroindole

Product 1

HCID 154534685-amino-1H-indole-7-carbonitrileYield 100.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 7-cyano-5-nitroindole (1.5 g, 8.2 mmol), hydrazine (1.0 mL, 31.2 mmol) and 10% Pd/C (20 mg) in 30 mL of MeOH was stirred at reflux for 2 h. The reaction mixture was filtered and concentrated in vacuo to provide 1.3 g (>95%) of the amine.

Workup

  1. temperatureat reflux for 2 h
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2f7f1f26184c4d76891104313b89774a
Source dataset
uspto-grants-2004_04
Patent number
US06723741B2

Reaction notes

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