6-Bromo-4-nitro-1H-indole → 4-Amino-6-bromoindole

HRID 1052531Notes

Reaction equation

HRID 1052531 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[C:4]([N+:11]([O-])=O)[CH:3]=1>C(O)(=O)C.[Fe]>[Br:1][C:2]1[CH:3]=[C:4]([NH2:11])[C:5]2[CH:6]=[CH:7][NH:8][C:9]=2[CH:10]=1

Participants

4

Reactant 1

HCID 247287506-Bromo-4-nitro-1H-indole

Product 1

HCID 105126634-Amino-6-bromoindoleYield 119.9%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

6-Bromo-4-nitro-1H-indole (1 g, 4.15 mmol) was treated with iron powder (1.16 g, 20 mmol) in acetic acid (60 ml) and stirred at room temperature. After 1 h the crude was filtered over Celite and the solvent was removed under reduced pressure. A mixture of a solution of sodium bicarbonate (4%) and ethyl acetate was added and the resulting mixture was filtered over Celite. The organic phase was washed with water and brine, dried over magnesium sulphate and the solvent was removed to give 1.05 g (100% yield) of the title compound as a dark solid, that was used in the next step without further purification. Purity 83%.

Workup

  1. filtrationAfter 1 h the crude was filtered over Celite
  2. customthe solvent was removed under reduced pressure
  3. additionA mixture of a solution of sodium bicarbonate (4%) and ethyl acetate
  4. additionwas added
  5. filtrationthe resulting mixture was filtered over Celite
  6. washThe organic phase was washed with water and brine
  7. dry with materialdried over magnesium sulphate
  8. customthe solvent was removed

Sources & evidence

ORD record
ord-0ff2c031d35f4db3aa1d6af2a331fb2b
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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