7-bromo-5-nitro-1H-indole → 7-Bromo-1H-indol-5-amine

HRID 583178Notes

Reaction equation

HRID 583178 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>C(O)(=O)C.[Zn]>[NH2:11][C:4]1[CH:5]=[C:6]2[C:10](=[C:2]([Br:1])[CH:3]=1)[NH:9][CH:8]=[CH:7]2

Participants

4

Reactant 1

HCID 38603267-bromo-5-nitro-1H-indole

Product 1

HCID 154345007-Bromo-1H-indol-5-amine

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 7-bromo-5-nitro-1H-indole (prepared according to the procedure set forth in L. L. Melhado et al., Phytochemistry, 21, 2879 (1982)) (550 mg, 2.28 mmol) in glacial acetic acid (16 mL) was treated with zinc dust (700 mg, 10.7 mmol) for 2 hours at room temperature. The mixture was then filtered through a pad of Celite, the filtrate evaporated, and coevaporated several times with toluene. The residue was taken up in methylene chloride (with a small amount of methanol), washed with saturated NaHCO3 solution, dried (Na2SO4), and evaporated. Flash chromatography eluting with 20% ethyl acetate in hexane afforded 153 mg of the title compound.

Workup

  1. customprepared
  2. filtrationThe mixture was then filtered through a pad of Celite
  3. customthe filtrate evaporated
  4. washwashed with saturated NaHCO3 solution
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. washFlash chromatography eluting with 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-ebb0ecddf67a43db880c9b1b00b1e28a
Source dataset
uspto-grants-1999_07
Patent number
US05929094

Reaction notes

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