Chloroform → 7-Bromo-1H-indol-5-amine

HRID 2086036Notes

Reaction equation

HRID 2086036 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:11]([O-])=O)[CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2.NN.C(Cl)(Cl)Cl>C(O)(C)C.[Pd]>[Br:1][C:2]1[CH:3]=[C:4]([NH2:11])[CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2

Participants

6

Reactant 3

HCID 6212ChloroformHCID 9321HydrazineHCID 38603267-bromo-5-nitro-1H-indole

Product 1

HCID 154345007-Bromo-1H-indol-5-amineYield 71.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

A solution of 7-bromo-5-nitroindole (0.68 g, 2.8 mmol), hydrazine (1.0 mL, 31 mmol) and 10% Pd/C (50 mg) in 50 mL of isopropanol was stirred at reflux for 2 h. The reaction mixture was filtered and concentrated in vacuo, yielding oily residue which was subjected to column chromatography (CHCl3, neat) to produce 0.41 g (2.0 mmol, 70%) of the desired product.

Workup

  1. temperatureat reflux for 2 h
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated in vacuo
  4. customyielding oily residue which

Sources & evidence

ORD record
ord-92c4c23e05c046e5b4e8d482ab77e1e7
Source dataset
uspto-grants-2004_04
Patent number
US06723741B2

Reaction notes

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