7-Chloro-5-nitro-1H-indole → HCID 15453465, compound

HRID 418551Notes

Reaction equation

HRID 418551 reaction equation
[Cl: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>CCO.[Pd]>[Cl: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

4

Reactant 1

HCID 154534647-Chloro-5-nitro-1H-indole

Product 1

HCID 15453465HCID 15453465, compoundYield 99.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Pd/C (DeGussa catalyst) (192 mg) was added to a solution of 7-chloro-5-nitro-1H-indole (Synthesis 2004, 4, 610-618) (765 mg, 3.9 mmol) in EtOH (15 mL) at room temperature and the reaction mixture was stirred under hydrogen atmosphere (1 atm.) for 3 hours. The catalyst was then filtered off on a celite pad and the filtrate was evaporated under reduced pressure to give a dark oil. This crude material was purified by flash chromatography (0% to 20% of MeOH in DCM) to give 648 mg (60% yield) of 7-chloro-1H-indol-5-ylamine.

Workup

  1. filtrationThe catalyst was then filtered off on a celite pad
  2. customthe filtrate was evaporated under reduced pressure
  3. customto give a dark oil
  4. customThis crude material was purified by flash chromatography (0% to 20% of MeOH in DCM)

Sources & evidence

ORD record
ord-c6b18a8e62324085a344471234452d33
Source dataset
uspto-grants-2012_01
Patent number
US08093285B2

Reaction notes

Loading…